Premium
Synthesis of stable and radioisotopomers of Taxa‐4(5),11(12)‐diene, Taxa‐4(20), 11(12)‐diene and Taxa‐4(20), 11(12)‐dien‐5‐α‐ol, early intermediates in taxol ® biosynthesis
Author(s) -
Rubenstein Steven M.,
Vazquez Alfredo,
SanzCervera Juan F.,
Williams Robert M.
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(200004)43:5<481::aid-jlcr334>3.0.co;2-o
Subject(s) - diene , ketone , taxon , chemistry , enone , stereochemistry , botany , organic chemistry , biology , natural rubber
The synthesis of [20‐C 2 H 3 ]‐Taxa‐4(5), 11(12)‐diene ( 3b ), [20‐C 2 H 2 ]‐Taxa‐4(20), 11(12)‐diene ( 7b ), [20‐ 3 H 3 ]‐Taxa‐4(5), 11(12)‐diene ( 3c ), [20‐ 3 H 2 ]‐Taxa‐4(20), 11(12)‐diene, ( 7c ), [20‐C 3 H 2 ]‐Taxa‐4(20), 11(12)‐diene‐5‐α‐ol ( 4b ), [20‐ 13 CH 2 ]‐Taxa‐4(20), 11(12)‐diene ( 7d ) and [20‐ 13 CH 3 ]‐taxa‐4(5), 11(12)‐diene ( 3d ) from the previously reported ketone 6 is described. Grignard addition to ketone provides the tertiary carbinols 8 which were dehydrated to a mixture of 3 and 7 . Alternatively, 7 can be prepared directly from ketone 6 by Wittig olefination. Copyright © 2000 John Wiley & Sons, Ltd.