Pentacyclic Steroids. 5. Total Synthesis of 4, 6β-Ethano-3-methoxy-8α-estra-1, 3, 5(10)-trien-17β- and 4, 6α-Ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one

Anil C. Ghosh; Braja G. Hazra; Karup Nielsen Ivan; Michael J. Kane; David Hawke; William L. Duax; Charles M. Weeks

doi:10.1021/jo01319a004

Pentacyclic Steroids. 5. Total Synthesis of 4, 6β-Ethano-3-methoxy-8α-estra-1, 3, 5(10)-trien-17β- and 4, 6α-Ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one

Anil C. Ghosh
, Braja G. Hazra
, Karup Nielsen Ivan
, Michael J. Kane
, David Hawke
, William L. Duax
, Charles M. Weeks

Department of Structural Biology

Incorporated
Hauptman-Woodward Medical Research Institute, Inc.

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Total synthesis of the novel pentacyclic steroids 4, 6β-ethano-3-methoxy-8α-estra-1, 3.5(10)-trien-17β-ol (5) and 4.6α-ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one (20) is described. -Methoxy-1 -tetralone (6) was converted in several steps into the key intermediate 8-methoxy-2α, 3, 4, 5-tetrahydro-5-acenaphthenone (14). The latter ketone was converted into 4, 6-ethano-3-methoxy-8(14)-seco-1, 3, 5(101, 9(11)-estratetraene-14, 17-dione (17) via the isothiouronium acetate (16).

Original language	English
Pages (from-to)	683-688
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	44
Issue number	5
DOIs	https://doi.org/10.1021/jo01319a004
State	Published - 1979

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@article{926bee7bb6534fb5ae599bf78d02c754,

title = "Pentacyclic Steroids. 5. Total Synthesis of 4, 6β-Ethano-3-methoxy-8α-estra-1, 3, 5(10)-trien-17β- and 4, 6α-Ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one",

abstract = "Total synthesis of the novel pentacyclic steroids 4, 6β-ethano-3-methoxy-8α-estra-1, 3.5(10)-trien-17β-ol (5) and 4.6α-ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one (20) is described. -Methoxy-1 -tetralone (6) was converted in several steps into the key intermediate 8-methoxy-2α, 3, 4, 5-tetrahydro-5-acenaphthenone (14). The latter ketone was converted into 4, 6-ethano-3-methoxy-8(14)-seco-1, 3, 5(101, 9(11)-estratetraene-14, 17-dione (17) via the isothiouronium acetate (16).",

author = "Ghosh, \{Anil C.\} and Hazra, \{Braja G.\} and Ivan, \{Karup Nielsen\} and Kane, \{Michael J.\} and David Hawke and Duax, \{William L.\} and Weeks, \{Charles M.\}",

year = "1979",

doi = "10.1021/jo01319a004",

language = "English",

volume = "44",

pages = "683--688",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Pentacyclic Steroids. 5. Total Synthesis of 4, 6β-Ethano-3-methoxy-8α-estra-1, 3, 5(10)-trien-17β- and 4, 6α-Ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one

AU - Ghosh, Anil C.

AU - Hazra, Braja G.

AU - Ivan, Karup Nielsen

AU - Kane, Michael J.

AU - Hawke, David

AU - Duax, William L.

AU - Weeks, Charles M.

PY - 1979

Y1 - 1979

N2 - Total synthesis of the novel pentacyclic steroids 4, 6β-ethano-3-methoxy-8α-estra-1, 3.5(10)-trien-17β-ol (5) and 4.6α-ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one (20) is described. -Methoxy-1 -tetralone (6) was converted in several steps into the key intermediate 8-methoxy-2α, 3, 4, 5-tetrahydro-5-acenaphthenone (14). The latter ketone was converted into 4, 6-ethano-3-methoxy-8(14)-seco-1, 3, 5(101, 9(11)-estratetraene-14, 17-dione (17) via the isothiouronium acetate (16).

AB - Total synthesis of the novel pentacyclic steroids 4, 6β-ethano-3-methoxy-8α-estra-1, 3.5(10)-trien-17β-ol (5) and 4.6α-ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one (20) is described. -Methoxy-1 -tetralone (6) was converted in several steps into the key intermediate 8-methoxy-2α, 3, 4, 5-tetrahydro-5-acenaphthenone (14). The latter ketone was converted into 4, 6-ethano-3-methoxy-8(14)-seco-1, 3, 5(101, 9(11)-estratetraene-14, 17-dione (17) via the isothiouronium acetate (16).

UR - https://www.scopus.com/pages/publications/0018397448

U2 - 10.1021/jo01319a004

DO - 10.1021/jo01319a004

M3 - Article

AN - SCOPUS:0018397448

SN - 0022-3263

VL - 44

SP - 683

EP - 688

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Pentacyclic Steroids. 5. Total Synthesis of 4, 6β-Ethano-3-methoxy-8α-estra-1, 3, 5(10)-trien-17β- and 4, 6α-Ethano-3-methoxyestra-1, 3, 5(10), 8, 14-pentaen-17-one

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