Journal
ORGANIC LETTERS
Volume 19, Issue 7, Pages 1698-1701Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00418
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Funding
- Department of Defense (DoD) through the National Defense Science & Engineering Graduate Fellowship Program
- NSF Graduate Research Fellowship Program [DGE-0703267]
- Swiss National Science Foundation
- NIH [NIGMS RGM097582A]
- American Cancer Society
- Research Corporation Cottrell Scholar program
- DuPont
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The first enantioSeleCtive total Synthesis of the epipolythiodiketopiperazine (ETP) natural product (-)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (-)-eniethalliein E and (-)-haernotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.
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