Synthesis 2016; 48(11): 1630-1636
DOI: 10.1055/s-0035-1561592
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Total Syntheses of the trans-2-Aryl-6-alkyltetrahydropyrans Diospongin B and Parvistones D and E from a Common Precursor

Zhilong Li
a  Department of Chemistry, Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, P. R. of China
,
Rongbiao Tong*
a  Department of Chemistry, Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, P. R. of China
b  HKUST Shenzhen Research Institute, Shenzhen 518057, P. R. of China   Email: rtong@ust.hk
› Author Affiliations
Further Information

Publication History

Received: 12 January 2016

Accepted after revision: 02 March 2016

Publication Date:
12 April 2016 (eFirst)

Abstract

Asymmetric total syntheses of diospongin B and parvistones D and E are reported. Our strategy features a high-yielding three-step reaction sequence: Achmatowicz rearrangement, reductive γ-deoxygenation, and Matsuda–Heck coupling to construct the rare and challenging trans-2-aryl-6-alkyltetrahydropyrans, which serve as common intermediates for the syntheses of diospongin B, and parvistones D and E.

Supporting Information

 
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