Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 52, Pages 17938-17954Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja806981k
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Funding
- National Science Foundation
- Bristol-Myers Squibb
- Scripps Research Institute
- Daiichi-Sankyo Co.
- Helsinki University of Technology
- Universidad Autonoma de Madrid
- Amgen
- AstraZeneca
- Beckman Foundation
- DuPont
- Eli Lilly
- GlaxoSmithKline
- Pfizer
- Roche
- Searle Scholarship Fund
- Sloan Foundation
- NIH (NIGMS)
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Full details are provided for the total synthesis of several members of the hapalindole family of natural products, including hapalindole Q, 12-epi-hapalindole D, 12-epi-fischerindole U, 12-epi-fischerindole G, 12-epi-fischerindole 1, and welwitindolinone A. Use of the recently developed direct indole coupling enabled an efficient, practical, scalable, and protecting-group-free synthesis of each of these natural products. The original biosynthetic proposal is reviewed, and a revised biosynthetic hypothesis is suggested, validated by the above syntheses. The syntheses are also characterized by an adherence to the concept of redox economy. Analogous to atom economy or step economy, redox economy minimizes the superfluous redox manipulations within a synthesis; rather, the oxidation state of intermediates linearly and steadily increases throughout the course of the synthesis.
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