97614-63-6Relevant academic research and scientific papers
Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings
Ploypradith, Poonsakdi,Petchmanee, Thaninee,Sahakitpichan, Poolsak,Litvinas, Nichole D.,Ruchirawat, Somsak
, p. 9440 - 9448 (2007/10/03)
(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.
Metabolites of the Marine Prosobranch Mollusc Lamellaria sp.
Andersen, Raymond J.,Faulkner, D. John,Cun-heng, He,Duyne, Gregory D. Van,Clardy, Jon
, p. 5492 - 5495 (2007/10/02)
The marine prosobranch mollusc, Lamellaria sp. contains four aromatic metabolites, lamellarins A-D (1-4).The structure of lamellarin A (1) was determined by an X-ray crystallographic study and the structures of lamellarins B-D (2-4) were assigned by inter
