White, James D.; Lincoln, Christopher M.; Yang, Jongtae; Martin, William H. C.; Chan, David B. published the artcile< Total Synthesis of Solandelactones A, B, E, and F Exploiting a Tandem Petasis-Claisen Lactonization Strategy>, Application In Synthesis of 617-55-0, the main research area is solandelactone A B E F total synthesis; Petasis Claisen lactonization tandem total synthesis solandelactone; Nozaki Hiyama Kishi coupling total synthesis solandelactone; Simmons Smith cyclopropanation total synthesis solandelactone; methylenation Petasis total synthesis solandelactone.
Solandelactones A, B, E, and F I (R = α-OH, R1 = H; R = β-OH, R1 = H; R = α-OH, R12 = bond; R = β-OH, R12 = bond, resp.) were synthesized using Nozaki-Hiyama-Kishi coupling of iododiene (3S,1E,5Z)-ICH:CHCH(OH)CH2CH:CH(CH2)4Me with aldehydes II obtained by oxidation of the corresponding alcs. Key steps in the synthesis of the latter alcs. (i) a Nagao asym. acetate aldol reaction of aldehyde (E)-Me3CPh2SiOCH2CH:CHCHO with thionothiazolidine III to set in place an alc. that becomes the (7S) lactone center of solandelactones, (ii) a Simmons-Smith cyclopropanation of (3R,4E)-Me3CPh2SiOCH2CH:CHCH(OH)CH2CON(MeO)Me directed by this alc., and (iii) Petasis methylenation of cyclic carbonate IV in tandem with a Claisen rearrangement that generates the octenalactone portion of solandelactones. Synthesis of solandelactones A, B, E, and F confirmed their gross structure and absolute configuration at C7, 8, 10, and 14 but showed that alc. configuration at C11 must be reversed in pairs, A/B and E/F, from the previous assignment made to these hydroid metabolites. A biogenesis of solandelactones is proposed for these C22 oxylipins that parallels a hypothesis put forward previously to explain the origin of C20 cyclopropane-containing algal products.
Journal of Organic Chemistry published new progress about Aldol addition, stereoselective (Nagao). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application In Synthesis of 617-55-0.
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