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

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

Pure And Applied Chemistry

Research output: Contribution to conference › Abstract

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)]

Original language	Undefined/Unknown
Pages	ORGN-027
Publication status	Published - 2000
Event	219th Meeting of the American Chemical Society - San Francisco, United States Duration: 26 Mar 2000 → 30 Mar 2000

Conference

Conference	219th Meeting of the American Chemical Society
Country	United States
City	San Francisco
Period	26/03/00 → 30/03/00

Keywords

synthesis
24(s)
25-epoxycholesterol
efficient perparation
desmosterol

Cite this

@conference{479852ee2fc242d7af02d258154c3ea7,

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",

}

TY - CONF

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

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

Y2 - 26 March 2000 through 30 March 2000

ER -