Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 7, Pages 2872-2877Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b12647
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Funding
- Natural Science Foundation of China [21602100, 21522204, 21472081]
- Guangdong Science and Technology Department [2016A050503011]
- Shenzhen Science and Technology Innovation Committee [JCYJ20170817110130636, JCYJ20170412152454807, JSGG20160301103446375]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17213101, KQTD2016053117035204]
- Shenzhen Peacock Plan
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The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.
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