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Synlett 2020; 31(16): 1623-1628
DOI: 10.1055/s-0040-1707198
DOI: 10.1055/s-0040-1707198
letter
Synthetic Study on Lactonamycins, Part 2: Stereoselective Access to ABCD-Ring System
This work was supported by Grants-in-Aid from the Japan Society for the Promotion of Science (JSPS) (Nos. JP16H06351 and JP18K06548).Further Information
Publication History
Received: 28 May 2020
Accepted after revision: 18 June 2020
Publication Date:
21 July 2020 (online)
Dedicated to the memory of Prof. Hidetoshi Yamada
Abstract
Toward a stereoselective total synthesis of the lactonamycins, we recently reported an approach to the DEF-ring system. Here we report a model study for constructing the ABCD-ring system, revealing a viable approach through (1) construction of the C-ring by asymmetric benzoin cyclization, (2) introduction of an angular hydroxy group through oxidation of an isoxazolium salt, and (3) construction of the AB rings through a ring-opening/closing sequence.
Key words
natural products - total synthesis - lactonamycins - aromatic polyketides - isoxazoles - benzoin cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707198.
- Supporting Information
-
References and Notes
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For a review, see: