Further studies on synthesis of 24(S),25-epoxycholesterol: new efficient preparation of desmosterol

Jr. Spencer Thomas A., Dansu Li, Jonathon S. Russel, Nicholas C. O. Tomkinson, Timothy M. Willson

Research output: Contribution to conferenceAbstract

Abstract

Our synthesis of the regulatory oxysterol 24(S),25-epoxycholesterol (1) from stigmasterol has been improved by the discovery that cuprate 2 can be coupled with allylic acetate 3 to give in 73% yield in the key step of the most effecient conversion yet of a C22 intermediate to desmosteryl acetate (4). Efforts to prep. diol 5 from sulfone 6 via Payne rearrangement of epoxide 7 will also be presented. [on SciFinder(R)]
LanguageUndefined/Unknown
PagesORGN-027
Publication statusPublished - 2000
Event219th Meeting of the American Chemical Society - San Francisco, United States
Duration: 26 Mar 200030 Mar 2000

Conference

Conference219th Meeting of the American Chemical Society
CountryUnited States
CitySan Francisco
Period26/03/0030/03/00

Keywords

  • synthesis
  • 24(s)
  • 25-epoxycholesterol
  • efficient perparation
  • desmosterol

Cite this

Spencer Thomas A., J., Li, D., Russel, J. S., Tomkinson, N. C. O., & Willson, T. M. (2000). Further studies on synthesis of 24(S),25-epoxycholesterol: new efficient preparation of desmosterol. ORGN-027. Abstract from 219th Meeting of the American Chemical Society, San Francisco, United States.
Spencer Thomas A., Jr. ; Li, Dansu ; Russel, Jonathon S. ; Tomkinson, Nicholas C. O. ; Willson, Timothy M. / Further studies on synthesis of 24(S),25-epoxycholesterol : new efficient preparation of desmosterol. Abstract from 219th Meeting of the American Chemical Society, San Francisco, United States.
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title = "Further studies on synthesis of 24(S),25-epoxycholesterol: new efficient preparation of desmosterol",
abstract = "Our synthesis of the regulatory oxysterol 24(S),25-epoxycholesterol (1) from stigmasterol has been improved by the discovery that cuprate 2 can be coupled with allylic acetate 3 to give in 73{\%} yield in the key step of the most effecient conversion yet of a C22 intermediate to desmosteryl acetate (4). Efforts to prep. diol 5 from sulfone 6 via Payne rearrangement of epoxide 7 will also be presented. [on SciFinder(R)]",
keywords = "synthesis, 24(s), 25-epoxycholesterol, efficient perparation, desmosterol",
author = "{Spencer Thomas A.}, Jr. and Dansu Li and Russel, {Jonathon S.} and Tomkinson, {Nicholas C. O.} and Willson, {Timothy M.}",
note = "CAPLUS AN 2000:332149(Conference; Meeting Abstract); null ; Conference date: 26-03-2000 Through 30-03-2000",
year = "2000",
language = "Undefined/Unknown",
pages = "ORGN--027",

}

Spencer Thomas A., J, Li, D, Russel, JS, Tomkinson, NCO & Willson, TM 2000, 'Further studies on synthesis of 24(S),25-epoxycholesterol: new efficient preparation of desmosterol' 219th Meeting of the American Chemical Society, San Francisco, United States, 26/03/00 - 30/03/00, pp. ORGN-027.

Further studies on synthesis of 24(S),25-epoxycholesterol : new efficient preparation of desmosterol. / Spencer Thomas A., Jr.; Li, Dansu; Russel, Jonathon S.; Tomkinson, Nicholas C. O.; Willson, Timothy M.

2000. ORGN-027 Abstract from 219th Meeting of the American Chemical Society, San Francisco, United States.

Research output: Contribution to conferenceAbstract

TY - CONF

T1 - Further studies on synthesis of 24(S),25-epoxycholesterol

T2 - new efficient preparation of desmosterol

AU - Spencer Thomas A., Jr.

AU - Li, Dansu

AU - Russel, Jonathon S.

AU - Tomkinson, Nicholas C. O.

AU - Willson, Timothy M.

N1 - CAPLUS AN 2000:332149(Conference; Meeting Abstract)

PY - 2000

Y1 - 2000

N2 - Our synthesis of the regulatory oxysterol 24(S),25-epoxycholesterol (1) from stigmasterol has been improved by the discovery that cuprate 2 can be coupled with allylic acetate 3 to give in 73% yield in the key step of the most effecient conversion yet of a C22 intermediate to desmosteryl acetate (4). Efforts to prep. diol 5 from sulfone 6 via Payne rearrangement of epoxide 7 will also be presented. [on SciFinder(R)]

AB - Our synthesis of the regulatory oxysterol 24(S),25-epoxycholesterol (1) from stigmasterol has been improved by the discovery that cuprate 2 can be coupled with allylic acetate 3 to give in 73% yield in the key step of the most effecient conversion yet of a C22 intermediate to desmosteryl acetate (4). Efforts to prep. diol 5 from sulfone 6 via Payne rearrangement of epoxide 7 will also be presented. [on SciFinder(R)]

KW - synthesis

KW - 24(s)

KW - 25-epoxycholesterol

KW - efficient perparation

KW - desmosterol

M3 - Abstract

SP - ORGN-027

ER -

Spencer Thomas A. J, Li D, Russel JS, Tomkinson NCO, Willson TM. Further studies on synthesis of 24(S),25-epoxycholesterol: new efficient preparation of desmosterol. 2000. Abstract from 219th Meeting of the American Chemical Society, San Francisco, United States.