Organometallic Routes to Novel Steroids Containing Heterocyclic C-17 Side-Chains

TY - JOUR

T1 - Organometallic Routes to Novel Steroids Containing Heterocyclic C-17 Side-Chains

AU - Vitellozzi, Lucia

AU - McAllister, Graeme D.

AU - Genski, Thorsten

AU - Taylor, Richard J K

N1 - © Georg Thieme Verlag. This is an author produced version of a paper published in Synthesis. Uploaded in accordance with the publisher's self-archiving policy.

PY - 2016/1/4

Y1 - 2016/1/4

N2 - A range of novel steroid analogues bearing a C-17 side-chain containing a 20R-hydroxyl group and a variety of heterocyclic substituents have been prepared by organometallic additions to 3-methoxypregnenolone. X-ray crystallography has been used to establish that the organometallic additions proceed with excellent Felkin-Anh control. This methodology has been extended, by use of the Achmatowicz rearrangement and ring-closing metathesis approaches, to prepare pyrandione and δ-lactone steroidal analogues reminiscent of the withanolide natural products.

AB - A range of novel steroid analogues bearing a C-17 side-chain containing a 20R-hydroxyl group and a variety of heterocyclic substituents have been prepared by organometallic additions to 3-methoxypregnenolone. X-ray crystallography has been used to establish that the organometallic additions proceed with excellent Felkin-Anh control. This methodology has been extended, by use of the Achmatowicz rearrangement and ring-closing metathesis approaches, to prepare pyrandione and δ-lactone steroidal analogues reminiscent of the withanolide natural products.

KW - Achmatowicz

KW - heterocycles

KW - metathesis

KW - organometallic

KW - steroid analogues

KW - withanolides

UR - http://www.scopus.com/inward/record.url?scp=84950281531&partnerID=8YFLogxK

U2 - 10.1055/s-0035-1560353

DO - 10.1055/s-0035-1560353

M3 - Article

AN - SCOPUS:84950281531

SN - 0039-7881

VL - 48

SP - 48

EP - 56

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 1

ER -