Intramolecular Diels-Alder Cycloaddition Approach toward the cis-Fused Δ5,6-Hexahydroisoindol-1-one Core of Cytochalasins

Jingjing Xu; Benguo Lin; Xiuqing Jiang; Zejun Jia; Jinlong Wu; Wei-Min Dai

doi:10.1021/acs.orglett.8b04129

Intramolecular Diels-Alder Cycloaddition Approach toward the cis-Fused Δ^5,6-Hexahydroisoindol-1-one Core of Cytochalasins

Org Lett. 2019 Feb 1;21(3):830-834. doi: 10.1021/acs.orglett.8b04129. Epub 2019 Jan 15.

Authors

Jingjing Xu^{1

2}, Benguo Lin¹, Xiuqing Jiang¹, Zejun Jia¹, Jinlong Wu¹, Wei-Min Dai^{1

3}

Affiliations

¹ Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry , Zhejiang University , Hangzhou 310027 , P. R. China.
² Department of Chemistry , Hangzhou Medical College , Hangzhou 310053 , P. R. China.
³ Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry , The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon , Hong Kong SAR , P. R. China.

PMID: 30645139
DOI: 10.1021/acs.orglett.8b04129

Abstract

Synthesis of the cis-fused Δ^5,6-hexahydroisoindol-1-one core of cytochalasins B₂-B₅, K, Z₈, Z₉, Z₁₂-Z₁₅, and Z₁₇ has been established starting from an intramolecular Diels-Alder reaction of the amide-tethered (8 E)-1,3,8-nonatriene. The trans-fused 5/6-bicyclic adduct was then subjected to highly stereoselective C9-β-hydroxylation and epimerization of the C7-α-OH group.

Publication types

Research Support, Non-U.S. Gov't