Barbatusin and cyclobutatusin, two novel diterpenoids from coleus barbatus bentham

Raymond Zelnik; David Lavie; Elie C. Levy; Andrew H.J. Wang; Iain C. Paul

doi:10.1016/0040-4020(77)88005-8

Barbatusin and cyclobutatusin, two novel diterpenoids from coleus barbatus bentham

Raymond Zelnik, David Lavie, Elie C. Levy, Andrew H.J. Wang, Iain C. Paul

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

39 Citations (Scopus)

Abstract

The structure of three diterpenoids from Coleus barbatus, Bentham (Labiatae) having a spirocyclopropyl side chain have been determined: they are barbatusin (1a), 3β-hydroxy-3-deoxybarbatusin (2) and cyclobutatusin (3a). The structures of 1a and 3a were established by X-ray diffraction analysis, and the latter compound has been shown to have an unusual 4-membered ring produced by a bond across C(1) to C(11). Chemical transformations and interconversions are presented, together with spectroscopic studies.

Original language	English
Pages (from-to)	1457-1467
Number of pages	11
Journal	Tetrahedron
Volume	33
Issue number	12
DOIs	https://doi.org/10.1016/0040-4020(77)88005-8
Publication status	Published - 1977
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4020(77)88005-8

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title = "Barbatusin and cyclobutatusin, two novel diterpenoids from coleus barbatus bentham",

abstract = "The structure of three diterpenoids from Coleus barbatus, Bentham (Labiatae) having a spirocyclopropyl side chain have been determined: they are barbatusin (1a), 3β-hydroxy-3-deoxybarbatusin (2) and cyclobutatusin (3a). The structures of 1a and 3a were established by X-ray diffraction analysis, and the latter compound has been shown to have an unusual 4-membered ring produced by a bond across C(1) to C(11). Chemical transformations and interconversions are presented, together with spectroscopic studies.",

author = "Raymond Zelnik and David Lavie and Levy, \{Elie C.\} and Wang, \{Andrew H.J.\} and Paul, \{Iain C.\}",

year = "1977",

doi = "10.1016/0040-4020(77)88005-8",

language = "English",

volume = "33",

pages = "1457--1467",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "12",

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T1 - Barbatusin and cyclobutatusin, two novel diterpenoids from coleus barbatus bentham

AU - Zelnik, Raymond

AU - Lavie, David

AU - Levy, Elie C.

AU - Wang, Andrew H.J.

AU - Paul, Iain C.

PY - 1977

Y1 - 1977

N2 - The structure of three diterpenoids from Coleus barbatus, Bentham (Labiatae) having a spirocyclopropyl side chain have been determined: they are barbatusin (1a), 3β-hydroxy-3-deoxybarbatusin (2) and cyclobutatusin (3a). The structures of 1a and 3a were established by X-ray diffraction analysis, and the latter compound has been shown to have an unusual 4-membered ring produced by a bond across C(1) to C(11). Chemical transformations and interconversions are presented, together with spectroscopic studies.

AB - The structure of three diterpenoids from Coleus barbatus, Bentham (Labiatae) having a spirocyclopropyl side chain have been determined: they are barbatusin (1a), 3β-hydroxy-3-deoxybarbatusin (2) and cyclobutatusin (3a). The structures of 1a and 3a were established by X-ray diffraction analysis, and the latter compound has been shown to have an unusual 4-membered ring produced by a bond across C(1) to C(11). Chemical transformations and interconversions are presented, together with spectroscopic studies.

UR - https://www.scopus.com/pages/publications/0017377708

UR - https://www.scopus.com/inward/citedby.url?scp=0017377708&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(77)88005-8

DO - 10.1016/0040-4020(77)88005-8

M3 - Article

AN - SCOPUS:0017377708

SN - 0040-4020

VL - 33

SP - 1457

EP - 1467

JO - Tetrahedron

JF - Tetrahedron

IS - 12

ER -

Barbatusin and cyclobutatusin, two novel diterpenoids from coleus barbatus bentham

Abstract

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