Paterson, Ian; Findlay, Alison D.; Noti, Christian published the artcile< Total synthesis of (-)-spirangien A, an antimitotic polyketide isolated from the myxobacterium Sorangium cellulosum>, SDS of cas: 617-55-0, the main research area is spirangien A preparation polyketide antimitotic antitumor agent asym synthesis.
An expedient first total synthesis of (-)-spirangien A, a potent cytotoxic and antifungal polyketide of myxobacterial origin, is described. A method for the synthesis of the title compound is reported here. By using a common 1,3-diol intermediate obtained by an efficient aldol-reduction sequence for installation of the C15-C18 and C25-C28 stereotetrads and a reagent-controlled boron aldol coupling followed by spiroacetalization, a highly convergent strategy was developed for construction of the elaborate spiroacetal core. Conversion of this advanced spiroacetal intermediate into (+)-spirangien diene, obtained previously by controlled degradation of spirangien A, was then achieved by installation of the truncated side-chain using an allylboration-Peterson sequence. The total synthesis of (-)-spirangien A was then achieved by the controlled attachment of the unsaturated C1-C12 side-chain, avoiding exposure to light. A Stork-Wittig olefination and double Stille cross-coupling sequence was exploited to install a delicate conjugated pentaene chromophore featuring alternating (Z)- and (E)-olefins, leading initially to the Me ester of spirangien A, which proved significantly more stable than the corresponding free acid. Subsequent careful hydrolysis afforded (-)-spirangien A. validating the relative and absolute configuration.
Chemistry – An Asian Journal published new progress about Absolute configuration. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, SDS of cas: 617-55-0.
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