Synthetic studies of trans-clerodane diterpenoids and congeners: stereocontrolled total synthesis of (.+-.)-avarol

1982 ◽  
Vol 47 (9) ◽  
pp. 1727-1731 ◽  
Author(s):  
Aluru S. Sarma ◽  
Partha Chattopadhyay
Keyword(s):  
Total Synthesis ◽  
Clerodane Diterpenoids ◽  
Synthetic Studies

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

1997 ◽  
Vol 75 (6) ◽  
pp. 646-655 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Kak-Shan Shia ◽  
Yongxin Han ◽  
Daqing Sun ◽  
Yu Wang
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Racemic Form ◽  
Diels Alder Reaction ◽  
Stereogenic Centers ◽  
The Face ◽  
Clerodane Diterpenoids ◽  
Synthetic Studies

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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