Standishinal, a novel carbon skeletal diterpene from the bark of Thuja standishii (Gord.) Carr

Standishinal ( 1), a new irregular abietane-type diterpenoid, was isolated from the bark of Thuja standishii and the absolute stereostructure was established by 2D NMR and X-ray crystallographic analyses. It was found that treatment of 12-hydroxy-6,7- seco-abieta-8,11,13-triene-6,7-dial ( 2) with BF...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 35; pp. 6419 - 6422
Main Authors Ohtsu, Hironori, Iwamoto, Manabu, Ohishi, Hirofumi, Matsunaga, Shunyo, Tanaka, Reiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.08.1999
Elsevier
Subjects
bark
chemical constituents of plants
chemical structure
Chemistry
Chemistry, Organic
diterpenoids
Physical Sciences
Science & Technology
stereochemistry
Thuja
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Summary:Standishinal ( 1), a new irregular abietane-type diterpenoid, was isolated from the bark of Thuja standishii and the absolute stereostructure was established by 2D NMR and X-ray crystallographic analyses. It was found that treatment of 12-hydroxy-6,7- seco-abieta-8,11,13-triene-6,7-dial ( 2) with BF 3·OEt 2 at 0°C in CH 2Cl 2 furnished compound 1. Standishinal ( 1), the first example of a 8-formyl-6(7→11) abeo-abietane was isolated from the bark of Thuja standishii. The absolute stereostructure of 1 was established by extensive NMR studies and X-ray analyses.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01191-0