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Diastereoselective Total Synthesis of (±)‐Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System
Author(s) -
Sun TianWen,
Ren WeiWu,
Xiao Qing,
Tang YeFeng,
Zhang YanDong,
Li Yong,
Meng FanKe,
Liu YiFan,
Zhao MingZhe,
Xu LingMin,
Chen JiaHua,
Yang Zhen
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200363
Subject(s) - moiety , annulation , salt metathesis reaction , total synthesis , chemistry , ring (chemistry) , metathesis , stereochemistry , bicyclic molecule , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization
First‐generation synthetic strategies for the diastereoselective total synthesis of schindilactone A ( 1 ) are presented and methods for the synthesis of the ABC, FGH, and CDEF moieties are explored. We have established a method for the synthesis of the ABC moiety, which included both a Diels–Alder reaction and a ring‐closing metathesis as the key steps. We have also developed a method for the synthesis of the FGH moiety, which involved the use of a Pauson–Khand reaction and a carbonylative annulation reaction as the key steps. Furthermore, we have achieved the construction of the central 7–8 bicyclic ring system by using a [3,3]‐rearrangement as the key step. However, unfortunately, when this rearrangement reaction was applied to the construction of the more advanced CDEF moiety, the anticipated annulation reaction did not occur and the development of an alternative synthetic strategy would be required for the construction of this central core.