Journal article
Stereospecific Access to α-Haloalkyl Esters via Enol Ester Epoxides and Synthesis of a C3–C21 Fragment of Bastimolide A
Organic & biomolecular chemistry, Vol.23(12), pp.2802-2806
03/28/2025
DOI: 10.1039/D5OB00070J
Appears in UI Libraries Support Open Access
Abstract
We report a 14-step synthesis of a C3–C21 fragment of bastimolides A and B, antimalarial macrocyclic polyketides. A crucial ring-opening reaction of an enol ester epoxide showed previously unexplored reactivity, leading to an asymmetric synthesis of α-haloalkyl esters. The α-haloalkyl ester synthesis was shown to be stereospecific, and provided access to a key α-silyloxyaldehyde to initiate application of configuration-encoded 1,5-polyol synthesis. This strategy established the C11/C15 and C15/C19 remote stereochemical relationships of the bastimolides. The potential of this C3–C21 fragment for coupling to C22–C41 was established using a Mukaiyama aldol reaction with a simple enolsilane.
Details
- Title: Subtitle
- Stereospecific Access to α-Haloalkyl Esters via Enol Ester Epoxides and Synthesis of a C3–C21 Fragment of Bastimolide A
- Creators
- Lucas W. HowellJacob N. HackbarthJeffrey S. AbrahamGregory K Friestad
- Resource Type
- Journal article
- Publication Details
- Organic & biomolecular chemistry, Vol.23(12), pp.2802-2806
- Publisher
- Royal Society of Chemistry
- DOI
- 10.1039/D5OB00070J
- ISSN
- 1477-0520
- eISSN
- 1477-0539
- Language
- English
- Electronic publication date
- 02/11/2025
- Date published
- 03/28/2025
- Academic Unit
- Chemistry
- Record Identifier
- 9984787235302771
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