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

31 December 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Iriomoteolide-13a
bis-THF ring system
syn-Oxypalladation
SN2 cyclization

Supplementary materials

Title
Description
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Title
SI-Irio-13a dai
Description
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