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Title: Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings
Authors: Poonsakdi Ploypradith
Thaninee Petchmanee
Poolsak Sahakitpichan
Nichole D. Litvinas
Somsak Ruchirawat
Chulabhorn Research Institute
The Institute of Science and Technology for Research and Development, Mahidol University
Stanford University
Keywords: Chemistry
Issue Date: 8-Dec-2006
Citation: Journal of Organic Chemistry. Vol.71, No.25 (2006), 9440-9448
Abstract: (Chemical Equation Presented) Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and α-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography. © 2006 American Chemical Society.
ISSN: 00223263
Appears in Collections:Scopus 2006-2010

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