Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 38, Pages 13226-13228Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja106739g
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Funding
- National Basic Research Program of China (973 Program) [2010CB833200]
- Chinese Academy of Sciences
- National Natural Science Foundation of China [20632050, 20921091]
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A concise asymmetric total synthesis of (-)-communesin F (similar to 6% overall yield in the longest linear sequence of 19 steps) is described. It features an unprecedented intramolecular oxidative coupling strategy for the elaboration of the requisite spiro-fused indoline moiety. Other notable elements are the use of TBS-protected (S)-phenylglycinol as a chiral auxiliary to induce the asymmetric formation of the spiro-fused indoline part, the mesylate-mediated formation of its G ring, and the introduction of the A ring at the final stage via intramolecular Staudinger reaction. This intramolecular Staudinger reaction proceeded smoothly at 80 degrees C, providing an additional example illustrating that twisted amides are more reactive than simple amides. Along with the total synthesis, we were able to assign the absolute configuration of natural communesin F as 6R,7R,8R,9S,11R.
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