Journal article
A Three-Step Catalytic Asymmetric Sequence from Alkynes to α-Silyloxyaldehydes and Its Application to a C22-C41 Fragment of Bastimolide A
Organic letters, Vol.26(21), pp.4492-4496
05/31/2024
DOI: 10.1021/acs.orglett.4c01310
PMCID: PMC11148846
PMID: 38753853
Appears in UI Libraries Support Open Access
Abstract
1,5-Polyol structures present challenges in stereocontrol, configurational assignment, and diastereomer separation; these are all compromised by remote stereochemical relationships. A configuration-encoded approach with alcohol configurations previously established within enantiopure building blocks offers a versatile solution to these issues. The iterative construction begins with α-silyloxyaldehydes; here, we introduce an enantioselective and step-economical route from alkynes to α-silyloxyaldehydes via silyl cation-induced ring opening of enol ester epoxides. This development enables an efficient configuration-encoded synthesis of the C22-C41 fragment of the bastimolides.
Details
- Title: Subtitle
- A Three-Step Catalytic Asymmetric Sequence from Alkynes to α-Silyloxyaldehydes and Its Application to a C22-C41 Fragment of Bastimolide A
- Creators
- Jacob N Hackbarth - University of IowaGregory K Friestad - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.26(21), pp.4492-4496
- Publisher
- American Chemical Society
- DOI
- 10.1021/acs.orglett.4c01310
- PMID
- 38753853
- PMCID
- PMC11148846
- eISSN
- 1523-7052
- Language
- English
- Electronic publication date
- 05/16/2024
- Date published
- 05/31/2024
- Academic Unit
- Chemistry
- Record Identifier
- 9984628218002771
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