The first stereoselective total synthesis of (Z)-cryptomoscatone D2, a natural G₂ checkpoint inhibitor

Gandolla Chinna Reddy; Penagaluri Balasubramanyam; N Salvanna; Thummala Sreenivasulu Reddy; Biswanath Das

doi:10.1016/j.bmcl.2012.02.025

The first stereoselective total synthesis of (Z)-cryptomoscatone D2, a natural G₂ checkpoint inhibitor

Bioorg Med Chem Lett. 2012 Apr 1;22(7):2415-7. doi: 10.1016/j.bmcl.2012.02.025. Epub 2012 Feb 17.

Authors

Gandolla Chinna Reddy¹, Penagaluri Balasubramanyam, N Salvanna, Thummala Sreenivasulu Reddy, Biswanath Das

Affiliation

¹ Organic Chemistry Division-I, Indian Institute of Chemical Technology (CSIR), Hyderabad 500 007, India.

PMID: 22405831
DOI: 10.1016/j.bmcl.2012.02.025

Abstract

The first stereoselective synthesis of (Z)-cryptomoscatone D2, a naturally occurring G(2) checkpoint inhibitor, was accomplished using propane-1,3-diol as the starting material. The Maruoka asymmetric allylation, ring closing metathesis and the hydrogenation of the triple bond employing Lindlar's catalyst were involved as the key steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / pharmacology
Catalysis
Cell Line, Tumor
Cryptocarya / chemistry
G2 Phase Cell Cycle Checkpoints / drug effects
Humans
Hydrogenation
Lactones / chemical synthesis*
Lactones / pharmacology
Molecular Structure
Propylene Glycols / chemistry*
Stereoisomerism

Substances

(Z)-cryptomoscatone D2
Antineoplastic Agents, Phytogenic
Lactones
Propylene Glycols