Studies toward the synthesis of the shark repellent pavoninin-5

Autor:	Deping Chai, Dominic Wright, Hua Gong, Wei Zhao, John R. Williams
Rok vydání:	2003
Předmět:	Cholesterol Ecology Chemistry Organic Chemistry Sharks Organic chemistry Animals Cell Biology Clemmensen reduction Biochemistry Deoxygenation Acetylglucosamine
Zdroj:	Lipids. 37(12)
ISSN:	0024-4201
Popis:	Sharks are the most dangerous predators of people in the sea, resulting in people being mauled and killed each year. A shark repellent could help to diminish this danger. The aglycone of the shark repellent pavoninin-5, (25R)-cholest-5-en-3beta,15alpha,26-triol (5a), was synthesized from diosgenin (9). Removing mercury from the Clemmensen reduction of 9 gave a higher yield of (25R)-cholest-5-en-3beta,16beta,26-triol, 10a, and was also more environmentally friendly. Attempted methods for the transposition of the C-16beta hydroxyl to the 15alpha position are described. A successful method for this transposition via the 15alpha-hydroxy-16-ketone, 8a, using the Barton deoxygenation reaction on the 16-alcohol 14b, is reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::63ca3290b18bc3c07311952091685681 https://pubmed.ncbi.nlm.nih.gov/12617474 Zobrazit plný text záznamu Full text from SpringerLink Plný text