5956-12-7Relevant academic research and scientific papers
Improved synthesis of (+)-dehydrobaimuximol, (-)-isobaimuxinol and (-)-baimuxinol from (-)-carvone
Chen,Shao,Li,Li
, p. 1061 - 1062 (2007/10/02)
An improved synthesis of (+)-dehydrobaimuxinol (1), (-)-isobaimuxinol (2) and (-)-baimuxinol (3) (2-hydroxymethyl-6,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodeca nes) has been described starting from (-)-carvone (p-mentha-6,8-dien-2-one) (4). The key step is the regiospecific allylic oxidation of α-agarofuran (7) by selenium(IV) oxide.
Stereoselective synthesis of dehydrobaimuxinol
Chen,Shao,Li,Li
, p. 1187 - 1189 (2007/10/02)
A stereoselective synthesis of dehydrobaimuxinol (1) is reported by employing an allylic oxidation as a key step.
Synthesis of Agarofurans by Cyclization of 10-Epieudesmene-3,11-diols
Huffman, John W.,Desai, Ranjit C.
, p. 3254 - 3258 (2007/10/02)
The course of the direct cyclization of 10-epi- and 14-nor-10-epieudesm-4-ene-3,11-diols (2, 5) to α-agarofuran (1) and its derivatives has been investigated in detail.The reaction of 10-epieudesm-4-ene-3α,11-diol (9) with Jones reagent, p-toluenesulfonic acid, diethyl azodicarboxylate-triphenylphosphine, or p-toluenesulfonyl chloride affords 1 in variable yields.The 3-epimer of diol 9 (8) also affords 1 under similar conditions.The 14-nor analogues of diols 8 and 9 (12, 13) were prepared and have been found to afford 14-nor-α-agarofuran (14) with p-toluenesulfonic acid and to afford mixtures containing variable amounts of 14 with Jones reagent.The preparation in good yield of 14-nor-9-oxo-α-agarofuran (4), an intermediate in the synthesis of polyhydroxyagarofurans, is described.The stereochemistry of diols 8 and 9 has been confirmed, and a variety of minor reaction products from the cyclizations reactions have been characterized.
