Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone

Mark J. Suto; Kenneth M. Tramposch; Mark Wierzba; Alan J. Solo; William Duax

doi:10.1021/jo00387a029

Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone

Mark J. Suto
, Kenneth M. Tramposch
, Mark Wierzba
, Alan J. Solo
, William Duax

Department of Structural Biology

SUNY Buffalo
Pfizer
Bristol-Myers Squibb

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

5 Scopus citations

Abstract

In an approach to the synthesis of ring C transposed progesterone derivatives rac-4,4-dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα:,10aβ)-perhydro-3-phenanthrenone (30) and rao7β,15α-ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione (28) have been synthesized from 6-methoxytetralone. The structure of 28 has been established by X-ray crystallographic analysis.

Original language	English
Pages (from-to)	2263-2273
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	52
Issue number	11
DOIs	https://doi.org/10.1021/jo00387a029
State	Published - May 1 1987

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Suto, M. J., Tramposch, K. M., Wierzba, M., Solo, A. J., & Duax, W. (1987). Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone. Journal of Organic Chemistry, 52(11), 2263-2273. https://doi.org/10.1021/jo00387a029

Suto, Mark J. ; Tramposch, Kenneth M. ; Wierzba, Mark et al. / Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone. In: Journal of Organic Chemistry. 1987 ; Vol. 52, No. 11. pp. 2263-2273.

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title = "Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone",

abstract = "In an approach to the synthesis of ring C transposed progesterone derivatives rac-4,4-dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα:,10aβ)-perhydro-3-phenanthrenone (30) and rao7β,15α-ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione (28) have been synthesized from 6-methoxytetralone. The structure of 28 has been established by X-ray crystallographic analysis.",

author = "Suto, \{Mark J.\} and Tramposch, \{Kenneth M.\} and Mark Wierzba and Solo, \{Alan J.\} and William Duax",

year = "1987",

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doi = "10.1021/jo00387a029",

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Suto, MJ, Tramposch, KM, Wierzba, M, Solo, AJ & Duax, W 1987, 'Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone', Journal of Organic Chemistry, vol. 52, no. 11, pp. 2263-2273. https://doi.org/10.1021/jo00387a029

Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone. / Suto, Mark J.; Tramposch, Kenneth M.; Wierzba, Mark et al.
In: Journal of Organic Chemistry, Vol. 52, No. 11, 01.05.1987, p. 2263-2273.

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

TY - JOUR

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AU - Suto, Mark J.

AU - Tramposch, Kenneth M.

AU - Wierzba, Mark

AU - Solo, Alan J.

AU - Duax, William

PY - 1987/5/1

Y1 - 1987/5/1

N2 - In an approach to the synthesis of ring C transposed progesterone derivatives rac-4,4-dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα:,10aβ)-perhydro-3-phenanthrenone (30) and rao7β,15α-ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione (28) have been synthesized from 6-methoxytetralone. The structure of 28 has been established by X-ray crystallographic analysis.

AB - In an approach to the synthesis of ring C transposed progesterone derivatives rac-4,4-dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα:,10aβ)-perhydro-3-phenanthrenone (30) and rao7β,15α-ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione (28) have been synthesized from 6-methoxytetralone. The structure of 28 has been established by X-ray crystallographic analysis.

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Suto MJ, Tramposch KM, Wierzba M, Solo AJ, Duax W. Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone. Journal of Organic Chemistry. 1987 May 1;52(11):2263-2273. doi: 10.1021/jo00387a029

Approaches to the Synthesis of Ring C Transposed Progesterone Analogues. rac -7β,15α-Ethano-11,12-seco-11,19-bisnor-17α-pregn-4-ene-3,20-dione and rac-4,4-Dimethyl-7,7-(ethylenedioxy)-(4aα,4bβ,8aα, 10aβ)-perhydro-3-phenanthrenone

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