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Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System
Author(s) -
Zhang JiaJun,
You Lin,
Wang YueFan,
Li YuanHe,
Liang XinTing,
Zhang Bo,
Yang ShouLiang,
Su Qi,
Chen JiaHua,
Yang Zhen
Publication year - 2016
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.201600130
Subject(s) - enantioselective synthesis , total synthesis , hydrogenolysis , intramolecular force , ring (chemistry) , chemistry , stereoselectivity , stereochemistry , combinatorial chemistry , catalysis , acetylene , kinetic resolution , organic chemistry
Abstract The enantioselective synthesis of the fully functionalized BCDE tetracyclic ring system of propindilactone G ( A ) is reported. Several synthetic methods were developed and applied to achieve this goal, including: 1) an asymmetric Diels–Alder reaction in the presence of Hayashi′s catalyst for the synthesis of optically pure key intermediate 3 ; 2) an intramolecular Pauson–Khand reaction (PKR) for the stereoselective synthesis of the BCDE ring with an all‐carbon chiral quaternary center at the C13 position by using the TMS‐substituted acetylene as the substrate; and 3) Pd‐catalyzed reductive hydrogenolysis for the stereoselective synthesis of the fully functionalized BCDE tetracyclic ring system. The chemistry developed herein provided a greater understanding of the total synthesis propindilactone G ( A ) and its analogues.