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Studies toward the synthesis of the shark repellent pavoninin‐5
Author(s) -
Williams John R.,
Chai Deping,
Gong Hua,
Zhao Wei,
Wright Dominic
Publication year - 2002
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-002-1020-1
Subject(s) - chemistry , diosgenin , triol , fatty alcohol , deoxygenation , aglycone , alcohol , ketone , organic chemistry , glycoside , diol , catalysis
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, (25 R )‐cholest‐5‐en‐3β,15α,26‐triol ( 5a ), was synthesized from diosgenin ( 9 ). Removing mercury from the Clemmensen reduction of 9 gave a higher yield of (25 R )‐cholest‐5‐en‐3β,16β,26‐triol, 10a , and was also more environmentally friendly. Attempted methods for the transposition of the C‐16β hydroxyl to the 15α position are described. A successful method for this transposition via the 15α‐hydroxy‐16‐ketone, 8a , using the Barton deoxygenation reaction on the 16‐alcohol 14b , is reported.