Total Synthesis and Cytotoxic Activity of 7-O-Methylnigrosporolide and Pestalotioprolide D

Author:

Tadpetch Kwanruthai1ORCID,Thiraporn Aticha1,Iawsipo Panata2

Affiliation:

1. Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University

2. Department of Biochemistry and Center of Excellence for Innovation in Chemistry, and Research Unit of Natural Bioactive Compounds for Healthcare Products ­Development, Faculty of Science, Burapha University

Abstract

AbstractA convergent total synthesis of 7-O-methylnigrosporolide and pestalotioprolide D has been accomplished in 17 linear steps and overall yields of 1.7% and 2.6%, respectively, starting from (S)-propylene oxide and (S)-benzyl glycidyl ether. Our synthesis exploited an acetylide addition and a Shiina macrolactonization to assemble the macrocycle, a Lindlar reduction, and Wittig and Still–Gennari olefinations to construct the three alkene groups, as well as a Jacobsen hydrolytic kinetic resolution to install the stereogenic center. The selection of the silyl protecting group of the C-4 alcohol was crucial for the final deprotection step. Our synthesis also led to a hypothesis that pestalotioprolide D might be an artifact of 7-O-methylnigrosporolide. The cytotoxic activities of the two synthetic compounds against six human cancer cell lines were evaluated. Synthetic pestalotioprolide D showed more potent cytotoxic activity than 7-O-methylnigrosporolide against all the cancer cell lines tested, and the SiHa cervical cancer cell line was the most sensitive to both synthetic compounds.

Funder

Thailand Science Research and Innovation

Prince of Songkla University

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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