Total Synthesis of (±)-Flustramines A and C, (±)-Flustramide A, and (−)- and (+)-Debromoflustramines A
Here we describe the efficient total synthesis of the three title hexahydropyrrolo[2,3-b]indole alkaloids and debromo derivative from readily available indolin-3-ones using key domino reactions, olefination−isomerization−Claisen rearrangement (OIC), and reductive cyclization (RC). (±)-Flustramine C...
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Published in: | Journal of organic chemistry 2008-08, Vol.73 (15), p.5959-5964 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | Here we describe the efficient total synthesis of the three title hexahydropyrrolo[2,3-b]indole alkaloids and debromo derivative from readily available indolin-3-ones using key domino reactions, olefination−isomerization−Claisen rearrangement (OIC), and reductive cyclization (RC). (±)-Flustramine C (5) was synthesized in five steps from 6-bromoindolin-3-one 9 via a key intermediate 13a. (±)-Flustramine A (1) has been obtained by reduction of flustramide A (6), which has been prepared in five steps from 13a. (±)-Debromoflustramine A (19) was provided in a similar manner from 13b. The (−)- and (+)-enantiomers of 19 were synthesized through optical resolution of (±)-carboxylic acid 17b using (R)-4-phenyloxazolidin-2-one. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo800984a |