Synlett 2022; 33(14): 1463-1467
DOI: 10.1055/s-0041-1737335
cluster
Organic Chemistry in Thailand

Asymmetric Formal Synthesis of (–)-Swainsonine from Chiral-Pool Precursors d-Mannose and d-Arabinose

Anphisa Lamor
,
Suwanan Uipanit
,
Sujitra Yakhampom
,
,
Ngampong Kongkathip
,
Boonsong Kongkathip
,
Financial support was provided by the Thailand Research Fund (MG6180015), the Kasetsart University Research and Development Institute (KURDI), the Graduate School Kasetsart University (through the Graduate School Fellowship Program), the Faculty of Science, Kasetsart University (through the PRF Funding), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Ministry of Higher Education, Science, Research and Innovation, Thailand, and the Department of chemistry, Kasetsart University.


Abstract

Carbohydrates have played an important role in organic synthesis. Since they contain many stereocenters, they have been widely used as chiral-pool starting materials. Herein, we report the asymmetric formal synthesis of (–)-swainsonine, which exhibits anticancer and immunosuppressive activities and inhibits lysosomal α-mannosidase activity, from d-mannose and d-arabinose. The synthesis utilized Zn-mediated Bernet–Vasella reaction, Horner–Wadsworth–Emmons olefination, and Grubbs olefin metathesis as key reactions.

Supporting Information



Publication History

Received: 12 December 2021

Accepted after revision: 12 January 2022

Article published online:
04 February 2022

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