Publication: Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings
Issued Date
2006-12-08
Resource Type
ISSN
00223263
Other identifier(s)
2-s2.0-33845530699
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Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.71, No.25 (2006), 9440-9448
Suggested Citation
Poonsakdi Ploypradith, Thaninee Petchmanee, Poolsak Sahakitpichan, Nichole D. Litvinas, Somsak Ruchirawat Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings. Journal of Organic Chemistry. Vol.71, No.25 (2006), 9440-9448. doi:10.1021/jo061810h Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/23138
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Title
Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings
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.