Total Synthesis of Cryptotrione
Mao‐Yun Lyu, Zhuliang Zhong, Vanessa Kar‐Yan Lo, Henry Ν. C. Wong, Xiao‐Shui Peng
Abstract
The total synthesis of cryptotrione (1) was enabled by substrate-controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum-catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane-type tricyclic diterpene skeleton. The stereogenic tertiary carbon center in the side chain was installed in a diastereodivergent manner by conjugate addition reactions.
Topics & Concepts
CycloisomerizationStereocenterChemistryAbietanePolyeneDiterpeneStereochemistryEnyneLewis acids and basesTotal synthesisConjugateEnantioselective synthesisCatalysisOrganic chemistryMathematicsMathematical analysisSynthetic Organic Chemistry MethodsCatalytic Alkyne ReactionsPhytochemical compounds biological activities