Stille/Diels-Alder reaction sequences: diversity-oriented access to novel steroids

Hans Wolf Sünnemann; Anja Hofmeister; Jörg Magull; Martin G Banwell; Armin de Meijere

doi:10.1021/ol062878m

Stille/Diels-Alder reaction sequences: diversity-oriented access to novel steroids

Org Lett. 2007 Feb 1;9(3):517-20. doi: 10.1021/ol062878m.

Authors

Hans Wolf Sünnemann¹, Anja Hofmeister, Jörg Magull, Martin G Banwell, Armin de Meijere

Affiliation

¹ Institut für Organische und Biomolekulare Chemie and Institut für Anorganische Chemie der Georg-August-Universität, Tammannstrasse 2-4, 37077 Göttingen, Germany.

PMID: 17249801
DOI: 10.1021/ol062878m

Abstract

[reaction: see text] An efficient, diversity-oriented approach to novel steroid analogues possessing a C-5beta configuration begins with the Stille cross-coupling of enantiomerically pure cycloalkenylstannane trans-2 and enol triflate 3. The resulting diene trans-4 engages in Diels-Alder cycloaddition reactions with a range of dienophiles to give, after removal of protecting groups, biologically interesting 6,7-disubstituted steroid analogues.

Publication types

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

MeSH terms

Alkadienes / chemistry
Cross-Linking Reagents / chemistry
Cyclization
Cycloparaffins / chemistry*
Mesylates / chemistry
Models, Chemical
Organometallic Compounds / chemistry*
Stereoisomerism
Steroids / chemical synthesis*
Tin Compounds / chemistry*

Substances

Alkadienes
Cross-Linking Reagents
Cycloparaffins
Mesylates
Organometallic Compounds
Steroids
Tin Compounds
stannane
trifluoromethanesulfonic acid