Redox approaches toward the synthesis of anti-cancer steroids: Ritterazine M and north unit of cephalostatin 1

Seongmin Lee, Purdue University

Abstract

Redox approaches toward the synthesis of anti-cancer steroidal spiroketals, such as ritterazines and cephalostatins, are described herein. (1) Redox refunctionalizaton of steroidal spiroketals was employed for the structure correction and total synthesis of ritterazine M. (2) An efficient protocol for introduction of C23 (R) alcohol in the cephalostatin intermediates is presented. (3) Cr[VI]-mediated C-H oxidations of non-activated hydrocarbons and steroidal cyclic ethers are depicted. (4) Various redox approaches, such as (i) C-H oxidation/Iodoetherification strategy; (ii) Alkoxy radical strategy; (iii) Diketone strategy; and (iv) Allylic oxidation strategy, were adopted to prepare north unit of cephalostatin 1.

Degree

Ph.D.

Advisors

Fuchs, Purdue University.

Subject Area

Organic chemistry

COinS