Issue 30, 2021

Enantioselective total synthesis of parnafungin A1 and 10a-epi-hirtusneanine

Abstract

The first and enantioselective total synthesis of the heterodimeric biaryl antifungal natural product parnafungin A1 as well as complex biaryl tetrahydroxanthone 10a-epi-hirtusneanine is accomplished, by employing cross-coupling through the benzoxaborole strategy to construct their sterically hindered biaryl cores. Besides the powerful Suzuki–Miyaura cross-coupling, the synthesis of parnafungin A1 also features a highly diastereoselective oxa-Michael addition to construct a tetrahydroxanthone skeleton, and an effective Zn-mediated reductive cyclization-Mitsunobu sequence to furnish the isoxazolidinone structure. Key innovations in total synthesis of 10a-epi-hirtusneanine include the employment of DTBS protection for functional group manipulation on the tetrahydroxanthone skeleton, stereoselective methylations, and complete reversal of the stereochemistry of the C5-hydroxy group using oxidation/Evans–Saksena reduction, as well as the strategy of preparing both complex tetrahydroxanthone monomers from the same chiral intermediate 25.

Graphical abstract: Enantioselective total synthesis of parnafungin A1 and 10a-epi-hirtusneanine

Supplementary files

Article information

Article type
Edge Article
Submitted
01 Jun 2021
Accepted
30 Jun 2021
First published
30 Jun 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 10313-10320

Enantioselective total synthesis of parnafungin A1 and 10a-epi-hirtusneanine

J. Sun, W. Gu, H. Yang and W. Tang, Chem. Sci., 2021, 12, 10313 DOI: 10.1039/D1SC02919C

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