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Chemistry. 2017 Oct 12;23(57):14182-14192. doi: 10.1002/chem.201702495. Epub 2017 Sep 7.

Modular Bi-Directional One-Pot Strategies for the Diastereoselective Synthesis of Structurally Diverse Collections of Constrained β-Carboline-Benzoxazepines.

Author information

1
Sharjah Institute for Medical Research, University of Sharjah, P.O.Box 27272, Sharjah, UAE.
2
Center for Systems Biology, Massachusetts General Hospital, Harvard Medical School, 185 Cambridge Street, Boston, MA, 02114, USA.
3
Harvard T.H. Chan School of Public Health, Department of Immunology and Infectious Disease, Boston, MA, 02115, USA.
4
Core Technologies Platform, New York University Abu Dhabi, P O Box 129188, Saadiyat Island, Abu Dhabi, UAE.
5
College of Pharmacy, University of Sharjah, P.O. Box 27272, Sharjah, UAE.

Abstract

The development of robust and efficient strategies to access structurally diverse drug-like compound collections remains an important challenge for small molecule probe development and drug discovery. Following a build/couple/pair strategy we have established bidirectional approach to unprecedented benzoxazepines by employing a Pictet-Spengler/aza-Michael addition cascade and Schiff base/aza-Michael addition/reduction protocols, respectively. The corresponding β-carboline-fused benzoxazepines and peripherally substituted benzoxazepines are isolated in high diastereoselectivity, good to excellent yields and have, to the best of our knowledge, never been reported.

KEYWORDS:

Pictet-Spengler reaction; aza-Michael addition; benzoxazepines; diversity oriented synthesis.; stereoselective synthesis

PMID:
28770556
DOI:
10.1002/chem.201702495

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