期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 30, 页码 10233-10235出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja103721s
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT) [15109001, 16073205, 20002004]
- Grants-in-Aid for Scientific Research [15109001, 16073205] Funding Source: KAKEN
A novel synthetic route to (+)-manzamine A was developed. It highlights an amazingly efficient construction of a highly strained 15-membered ring across a cyclohexenone ring with the aim of installing the requisite functionalities in a completely stereocontrolled manner. Other key features include a stereoselective Diels-Alder reaction of an optically active butenolide, construction of the 15-membered ring by intramolecular Mitsunobu reaction of a nosyl amide, [3,3]-sigmatropic rearrangement of allyl cyanate for stereoselective introduction of nitrogen functionality at a sterically congested position, and a ring-closing metathesis in the presence of labile functional groups.
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