Access to functionalized steroid side chains via modified Julia olefination.
Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.
Department of Chemistry, 207 Pleasant Street, SE, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Enver Cagri
EC
Izgu
Aaron C
AC
Burns
Thomas R
TR
Hoye
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D000475:Alkenes; D013256:Steroids; D013450:Sulfones
Steroids. 2002 Mar;67(3-4):291-304
11856553
Steroids. 2004 Apr;69(4):291-9
15183695
Steroids. 2000 Jul;65(7):401-7
10899540
Bioorg Med Chem. 2006 Mar 15;14(6):1761-70
16288879
Nat Chem Biol. 2005 Nov;1(6):324-8
16408070
J Org Chem. 2000 Apr 7;65(7):1919-23
10774010
Steroids. 1993 Aug;58(8):370-8
8212087
Proc Natl Acad Sci U S A. 1993 Feb 15;90(4):1354-8
8433993
Org Lett. 2000 Sep 21;2(19):2921-2
10986072
Bioorg Med Chem Lett. 2002 Feb 11;12(3):433-5
11814814
J Nat Prod. 2000 May;63(5):631-5
10843574
J Am Chem Soc. 2007 Aug 15;129(32):9866-7
17658816
J Am Chem Soc. 2001 Oct 31;123(43):10772-3
11674024
J Org Chem. 1997 Jun 27;62(13):4541-4545
11671794