Total syntheses of the monoterpene indole alkaloids (±)-alstilobanine A and E and (±)-angustilodine.
@article{Feng2014TotalSO, title={Total syntheses of the monoterpene indole alkaloids (±)-alstilobanine A and E and (±)-angustilodine.}, author={Y. Feng and M. M. Majireck and S. Weinreb}, journal={The Journal of organic chemistry}, year={2014}, volume={79 1}, pages={ 7-24 } }
A synthetic strategy has been developed culminating in stereoselective total syntheses of the small class of unusual monoterpenoid indole alkaloids exemplified by alstilobanines A (3) and E (2) and angustilodine (1). A pivotal step includes a novel intermolecular Michael-type addition of an indole ester dianion to a piperidine-derived nitrosoalkene to form the C15, C16 bond of the alkaloids. In addition, an application of the Romo protocol for effecting a stereoselective intramolecular… CONTINUE READING
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