5989-73-1Relevant academic research and scientific papers
Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols
Davis, Dexter C.,Walker, Katherine L.,Hu, Chunhua,Zare, Richard N.,Waymouth, Robert M.,Dai, Mingji
, p. 10693 - 10699 (2016/09/04)
A palladium-catalyzed cascade carbonylative spirolactonization of hydroxycyclopropanols has been developed to efficiently synthesize oxaspirolactones common to many complex natural products of important therapeutic value. The mild reaction conditions, high atom economy, broad substrate scope, and scalability of this new method were highlighted in expedient total syntheses of the Turkish tobacco natural products α-levantanolide and α-levantenolide in two and four steps, respectively. The hydroxycyclopropanol substrates are readily available in one step via a Kulinkovich reaction of the corresponding lactones. Mechanistic studies utilizing high-resolution electrospray ionization mass spectrometry (ESI-MS) identified several key intermediates in the catalytic cycle, as well as those related to catalyst decomposition and competitive pathways.
Chemistry of labdanediol from Cistus ladaniferus, L. synthesis of 12-Nor-ambreinolide and α and β-levantenolides
Urones,Basabe,Marcos,Diez Martin,Sexmero,Peral,Broughton
, p. 10389 - 10398 (2007/10/02)
Labdanediol, 2, the major component of the neutral part of Cistus ladaniferus L, was transformed into 12-nor-ambreinolide, precursor of ambrox, in three steps with an overall yield of 70%. Molecular modelling techniques have been used to determine the stereochemistry of the byproducts of these reactions. The selenylation and elimination reactions of α and βlevantanolides, obtained from labdanediol, 2, were used to synthetise α and β-levantenolides.
