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DOI RECORD

Asymmetric Total Synthesis of Speciosin B

Yo Kitazawa iD, Daisuke Ito, Hitoshi Otsuki iD, Tsuyoshi Ichiyanagi iD

DOI10.2139/ssrn.7593784

PublisherElsevier BV

Journal / Source—

Published2026

Metadata Deposited2026-10-10 (updated: 2026-10-10)

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Typeposted-content

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Citations0

References deposited15

Access / license metadataAccess not determined License 1 ↗A reuse license does not by itself establish whether the full text is freely readable.

Abstract

The asymmetric total synthesis of both diastereomers of speciosin B, each bearing a terminal epoxide, was achieved. Enantiomeric building blocks derived from D- and L-tartaric acid enabled the selective preparation of the R- and S-configured terminal epoxide variants, which were obtained in 21% and 22% overall yields, respectively, from D-quinic acid. A spectroscopic comparison of the synthetic and natural samples of Aporpium strigosum (TUFC 100651) revealed that the natural sample is a mixture of diastereomers.

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