Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins

Sitaram Pal; Sukumar Ghosh; Bimal K. Banik; Shaikh Khairul Alam; Usha Ranjan Ghatak

doi:10.1080/00397919008053160

Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins

Sitaram Pal, Sukumar Ghosh, Bimal K. Banik, Shaikh Khairul Alam, Usha Ranjan Ghatak

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

1 Scopus citations

Abstract

The bridged-ethers,(±) -2-methoxy-9a-carbamorphinan (lb) and (±)-2-methoxy-9a-carba-14α-morphinan(2b) have been synthesized. The acid-catalyzed cyclizations of 1-m-methoxy-benzyloctalone 3b and 1-m-methoxybenzyloctalins 4b proceed with high regio-and stereoselectivities leading mostly to the bridged-ketone 14 and ether lb respectively, along with o-methoxy-tetracyclic ketone 15 and the ether 17, in addition to other minor products.

Original language	English
Pages (from-to)	2203-2216
Number of pages	14
Journal	Synthetic Communications
Volume	20
Issue number	14
DOIs	https://doi.org/10.1080/00397919008053160
State	Published - 1 Jul 1990
Externally published	Yes

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Pal, S., Ghosh, S., Banik, B. K., Alam, S. K., & Ghatak, U. R. (1990). Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins. Synthetic Communications, 20(14), 2203-2216. https://doi.org/10.1080/00397919008053160

@article{eb615ef7ff05411b9066efc1c31d4215,

title = "Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins",

abstract = "The bridged-ethers,(±) -2-methoxy-9a-carbamorphinan (lb) and (±)-2-methoxy-9a-carba-14α-morphinan(2b) have been synthesized. The acid-catalyzed cyclizations of 1-m-methoxy-benzyloctalone 3b and 1-m-methoxybenzyloctalins 4b proceed with high regio-and stereoselectivities leading mostly to the bridged-ketone 14 and ether lb respectively, along with o-methoxy-tetracyclic ketone 15 and the ether 17, in addition to other minor products.",

author = "Sitaram Pal and Sukumar Ghosh and Banik, {Bimal K.} and Alam, {Shaikh Khairul} and Ghatak, {Usha Ranjan}",

year = "1990",

month = jul,

day = "1",

doi = "10.1080/00397919008053160",

language = "Ingl{\'e}s",

volume = "20",

pages = "2203--2216",

journal = "Synthetic Communications",

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Pal, S, Ghosh, S, Banik, BK, Alam, SK & Ghatak, UR 1990, 'Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins', Synthetic Communications, vol. 20, no. 14, pp. 2203-2216. https://doi.org/10.1080/00397919008053160

Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins. / Pal, Sitaram; Ghosh, Sukumar; Banik, Bimal K. et al.
In: Synthetic Communications, Vol. 20, No. 14, 01.07.1990, p. 2203-2216.

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

TY - JOUR

T1 - Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan

T2 - Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins

AU - Pal, Sitaram

AU - Ghosh, Sukumar

AU - Banik, Bimal K.

AU - Alam, Shaikh Khairul

AU - Ghatak, Usha Ranjan

PY - 1990/7/1

Y1 - 1990/7/1

N2 - The bridged-ethers,(±) -2-methoxy-9a-carbamorphinan (lb) and (±)-2-methoxy-9a-carba-14α-morphinan(2b) have been synthesized. The acid-catalyzed cyclizations of 1-m-methoxy-benzyloctalone 3b and 1-m-methoxybenzyloctalins 4b proceed with high regio-and stereoselectivities leading mostly to the bridged-ketone 14 and ether lb respectively, along with o-methoxy-tetracyclic ketone 15 and the ether 17, in addition to other minor products.

AB - The bridged-ethers,(±) -2-methoxy-9a-carbamorphinan (lb) and (±)-2-methoxy-9a-carba-14α-morphinan(2b) have been synthesized. The acid-catalyzed cyclizations of 1-m-methoxy-benzyloctalone 3b and 1-m-methoxybenzyloctalins 4b proceed with high regio-and stereoselectivities leading mostly to the bridged-ketone 14 and ether lb respectively, along with o-methoxy-tetracyclic ketone 15 and the ether 17, in addition to other minor products.

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U2 - 10.1080/00397919008053160

DO - 10.1080/00397919008053160

M3 - Artículo

SN - 0039-7911

VL - 20

SP - 2203

EP - 2216

JO - Synthetic Communications

JF - Synthetic Communications

IS - 14

ER -

Synthesis of (±)-2-methoxy-9a-carbamorphinan and (+) -2-methoxy-9a-carba-14α -morphinan: Acid catalyzed cyclizations of 1-m-methoxybenzyl-4, 4a,5,6,7, 8-hexahydronaphthalen-2 (3h)-one and 1-m-methoxybenzyloctalins

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