BIOMAT Database Logo BIOMAT Database Logo

Asymmetric synthesis of (+)-geranyllinaloisocyanide: assignment of absolute stereochemistry. 2011

Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Faculty of Science, Kochi University, Akebono-cho, Kochi, Japan. ichikawa@kochi-u.ac.jp

The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (-)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.

UI MeSH Term Description Entries
D008386 Marine Biology The study of the origin, structure, development, growth, function, genetics, and reproduction of organisms which inhabit the OCEANS AND SEAS. Biology, Marine,Marine Ecology,Marine Hydrobiology,Ecology, Marine,Hydrobiology, Marine
D009570 Nitriles Organic compounds containing the -CN radical. The concept is distinguished from CYANIDES, which denotes inorganic salts of HYDROGEN CYANIDE. Nitrile
D011161 Porifera The phylum of sponges which are sessile, suspension-feeding, multicellular animals that utilize flagellated cells called choanocytes to circulate water. Most are hermaphroditic. They are probably an early evolutionary side branch that gave rise to no other group of animals. Except for about 150 freshwater species, sponges are marine animals. They are a source of ALKALOIDS; STEROLS; and other complex molecules useful in medicine and biological research. Demospongiae,Sponges (Zoology),Sponge (Zoology),Sponges,Poriferas,Sponge
D004224 Diterpenes Twenty-carbon compounds derived from MEVALONIC ACID or deoxyxylulose phosphate. Diterpene,Diterpenes, Cembrane,Diterpenes, Labdane,Diterpenoid,Labdane Diterpene,Norditerpene,Norditerpenes,Norditerpenoid,Cembranes,Diterpenoids,Labdanes,Norditerpenoids,Cembrane Diterpenes,Diterpene, Labdane,Labdane Diterpenes
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D006254 Hawaii A group of islands in Polynesia, in the north central Pacific Ocean, comprising eight major and 114 minor islands, largely volcanic and coral. Its capital is Honolulu. It was first reached by Polynesians about 500 A.D. It was discovered and named the Sandwich Islands in 1778 by Captain Cook. The islands were united under the rule of King Kamehameha 1795-1819 and requested annexation to the United States in 1893 when a provisional government was set up. Hawaii was established as a territory in 1900 and admitted as a state in 1959. The name is from the Polynesian Owhyhii, place of the gods, with reference to the two volcanoes Mauna Kea and Mauna Loa, regarded as the abode of the gods. (From Webster's New Geographical Dictionary, 1988, p493 & Room, Brewer's Dictionary of Names, 1992, p2330) Midway Island,Midway Islands
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D019344 Lactic Acid A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed) Lactate,2-Hydroxypropanoic Acid,2-Hydroxypropionic Acid,Ammonium Lactate,D-Lactic Acid,L-Lactic Acid,Propanoic Acid, 2-Hydroxy-, (2R)-,Propanoic Acid, 2-Hydroxy-, (2S)-,Sarcolactic Acid,2 Hydroxypropanoic Acid,2 Hydroxypropionic Acid,D Lactic Acid,L Lactic Acid,Lactate, Ammonium

Related Publications

Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Assignment of absolute stereochemistry and total synthesis of (-)-spongidepsin.
June 2004, Organic letters,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Total synthesis, assignment of absolute stereochemistry, and structural revision of chlorofusin.
May 2007, Journal of the American Chemical Society,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Asymmetric synthesis of (+)- and (-)-pauciflorol F: confirmation of absolute stereochemistry.
August 2013, Organic letters,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
(-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment.
April 2017, Organic letters,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.
September 2001, Journal of the American Chemical Society,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Asymmetric Total Synthesis and Assignment of Absolute Configuration of Arbornamine.
November 2020, Organic letters,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Asymmetric total synthesis of (-)-lundurine B and determination of its absolute stereochemistry.
April 2015, Chemistry, an Asian journal,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
First enantioselective synthesis and absolute stereochemistry assignment of new monocyclic sesquiterpenes from Artemisia chamaemelifolia.
June 2003, The Journal of organic chemistry,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Asymmetric total synthesis of (-)-VM55599: establishment of the absolute stereochemistry and biogenetic implications.
March 2002, Journal of the American Chemical Society,
Yoshiyasu Ichikawa, and Yasunori Matsuda, and Ken Okumura, and Mitsuhiro Nakamura, and Toshiya Masuda, and Hiyoshizo Kotsuki, and Keiji Nakano
Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.
April 2012, Organic letters,
Copied contents to your clipboard!