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Synlett 2020; 31(09): 907-910
DOI: 10.1055/s-0039-1690829
letter
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of Pseudolaric Acid B

Naoki Mori  ∗
Research Foundation ITSUU Laboratory, C1232 Kanagawa Science Park R & D Building, 3-2-1 Sakado, Takatsu-ku, Kawasaki, Kanagawa 213-0012, Japan   eMail: nmori@itsuu.or.jp
› InstitutsangabenThis work was supported by Grant-in-Aid for Scientific Research (C) from the Japan Society for the Promotion of Science (Grant Number 16K07712).
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Publikationsverlauf

Received: 28. Dezember 2019

Accepted after revision: 02. Februar 2020

Publikationsdatum:
18. Februar 2020 (online)

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Abstract

A formal synthesis of pseudolaric acid B, a diterpene isolated from the root bark of Pseudolarix kaempferi Gordon (Pinaceae), to Trost’s synthetic intermediate was achieved in 17 steps from a known ketone. Key features of this synthesis include a Claisen rearrangement and iodoetherification to construct quaternary stereocenters and ring-closing metathesis to form the seven-membered ring.

Key words

pseudolaric acid B - total synthesis - diterpenes - cytotoxins - Claisen rearrangement - iodoetherification

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690829.
  • Supporting Information
 

  • References and Notes

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