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Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

preprint
submitted on 30.12.2020, 21:47 and posted on 31.12.2020, 11:44 by Hui Zhao, Kai Gao, Haichen Ma, Tsz Chun Yip, Wei-Min Dai
The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The w-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by anti-aldol reaction and asymmetric dihydroxylation (AD). Upon heating in pyridine the stereotetrad underwent an SN2 cyclization to form the C19–C22 THF ring. It was followed by an intramolecular syn-oxypalladation of the C28 chiral allylic alcohol to give the C23–C26 THF ring.

Funding

General Research Fund grant (16301315) from the Research Grant Council, The Hong Kong Special Administrative Region, P. R. China

The Hong Kong Branch of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (SMSEGL20SC01)

History

Email Address of Submitting Author

chdai@ust.hk

Institution

The Hong Kong University of Science and Technology

Country

P. R. of China

ORCID For Submitting Author

0000-0001-5688-7606

Declaration of Conflict of Interest

No conflict of interest

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