期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 12, 页码 2414-2421出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101603
关键词
Carbohydrates; Esterification; Metathesis; Macrocycles
资金
- Council of Scientific and Industrial Research, New Delhi, India [MLP-0010C]
- University Grants Commission (UGC), New Delhi, India
The total synthesis of macrosphelide M is described. The key steps include the preparation of the acid and alcohol fragments from diacetone glucose and (S)-malic acid, respectively, followed by Yamaguchi esterification and macrocyclization of the tris-olefin by ring-closing metathesis. Finally, one-pot deprotection of the PMB and TBS groups with TiCl4 results in the target. The C-3/C-4 stereocenters of diacetone glucose are used for the introduction of four stereocenters, whereas the fifth stereocenter is realized from (S)-malic acid.
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