MALAYSIAN JOURNAL OF CHEMISTRY (MJChem)

MJChem is double-blind peer reviewed journal published by the Malaysian Institute of Chemistry (Institut Kimia Malaysia) E-ISSN: 2550-1658

Asymmetric Synthesis of Hydroxy N,O-Heterobicyclic Octanes

Nur Shahidah Sharoman
Universiti Teknologi MARA
Syahrul Imran
Universiti Teknologi MARA
Mohd Tajudin Mohd Ali
Universiti Teknologi MARA

DOI: https://doi.org/10.55373/mjchem.v24i2.223

Keywords: N,O-heterobicyclic octane: anticancer; retronecine; cis-butyrolactone

Abstract

A new asymmetric synthesis of several hydroxy N,O-heterobicyclic octanes is described in this paper. The synthesis employed Salen catalysed epoxide ring opening of the starting material meso-cyclohexene followed by the azide reduction and NBoc protection of (1S,6S)-6-azido-3-cyclohexenol, allylic hydroxylation and lactonization with final carbonyl reduction to produce hydroxy N,O-heterobicyclic octane.

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Published 30 June 2022


Issue Vol 24 No 2 (2022): Malaysian Journal of Chemistry

Section