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Novel approach for the introduction of a C‐1 oxygenated group on the decalin skeleton: first asymmetric total synthesis of 1 S ,6 S ‐dihydroxy‐eudesm‐3‐ene
Author(s) -
Zheng Guojun,
Chen Jinchun,
Fang Lijing,
Guan Yukun,
Li Yulin
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20062
Subject(s) - chemistry , decalin , total synthesis , stereochemistry , aldol reaction , skeleton (computer programming) , natural product , ring (chemistry) , group (periodic table) , organic chemistry , catalysis , computer science , programming language
This paper describes a novel approach for the introduction of a C‐1 hydroxyl on the decalin ring system, starting from (−)‐carvone. Utilizing the substratecontrolled Mukaiyama aldol reaction and alkaline cyclization as key steps, the C‐1 oxygenated decalin eudesmane skeleton 2 ′ and its four isomers were synthesized efficiently. Furthermore, X‐ray structural analysis showed that the claimed structure for the natural product is incorrect. Chirality 16:483–485, 2004. © 2004 Wiley‐Liss, Inc.