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Synthesis 2023; 55(16): 2602-2608
DOI: 10.1055/a-2058-0355
paper
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

Synthesis of the C17–C30 Bis-THF Fragment of Iriomoteolide-13a via Intramolecular syn-Oxypalladation of 26-Ene-17,21,23,28-tetraol

Kai Gao
a   Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and 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. of China
b   School of Pharmaceutical Sciences, Taizhou University, Taizhou 318000, P. R. of China
,
Haichen Ma
a   Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and 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. of China
,
Tsz Chun Yip
a   Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and 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. of China
,
Hui Zhao
a   Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and 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. of China
,
Wei-Min Dai∗
a   Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and 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. of China
› Author AffiliationsThis work was supported in part by a General Research Fund grant (16301315) from the Research Grant Council, The Hong Kong Special Administrative Region, P. R. China and The Hong Kong Branch of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (SMSEGL20SC01).
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Dedicated to Prof. Guo-Qianq Lin of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences on the occasion of his 80th birthday

Abstract

The fully substituted C17–C30 bis-tetrahydrofuran fragment of the proposed structure of iriomoteolide-13a has been assembled via asymmetric dihydroxylation-SN2 cyclization of 19-mesyloxy-21-ene-26-yne and PdCl2-catalyzed syn-oxypalladation of 26-ene-17,21,23,28-tetraol as the key steps. The syn-oxypalladation process gave an 89:11 diastereoselectivity and tolerated the free poly-hydroxy groups in the highly functionalized substrate.

Key words

allylic alcohol - iriomoteolide-13a - oxypalladation - propargylic alcohol - bis-tetrahydrofuran

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2058-0355.
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Publication History

Received: 07 March 2023

Accepted after revision: 20 March 2023

Accepted Manuscript online:
20 March 2023

Article published online:
25 April 2023

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