Synthetic studies on clerodane diterpenoids. The total synthesis of (±)-2-oxo-5α,8α-13,14,15,16-tetranorclerod-3-en-12-oic acid | Zendy

HsingJang Liu | Zendy; KakShan Shia | Zendy; Yongxin Han | Zendy; Daqing Sun | Zendy; Yu Wang | Zendy

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Synthetic studies on clerodane diterpenoids. The total synthesis of (±)-2-oxo-5α,8α-13,14,15,16-tetranorclerod-3-en-12-oic acid

Author(s) -

HsingJang Liu,

KakShan Shia,

Yongxin Han,

Daqing Sun,

Yu Wang

Publication year - 1997

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v97-079

Subject(s) - chemistry , total synthesis , stereocenter , decalin , stereochemistry , adduct , diterpene , terpene , organic chemistry , enantioselective synthesis , catalysis

A general synthetic approach to diterpenoids of the cis-clerodane family has been developed, leading to the first total synthesis, in racemic form, of 2-oxo-5α,8α-13,14,15,16-tetranorclerod-3-en-12-oic acid (2). The key operation involved is the face-selective Diels–Alder reaction of dienone ester 10 with trans-piperylene, giving rise to adduct 11 containing the decalin nucleus and correct stereogenic centers common to many cis-clerodane diterpenoids. Keywords: cis-clerodanes, general synthetic approach, total synthesis, face-selective Diels–Alder reaction.

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