The stereocontrolled synthesis of the C（17）--C（28） fragment 3 of didemnaketal B was accomplished in 21 steps from the natural （R）-（＋）-pulegone and （S）-（--）-citronellal. The key steps involved diastereosel...The stereocontrolled synthesis of the C（17）--C（28） fragment 3 of didemnaketal B was accomplished in 21 steps from the natural （R）-（＋）-pulegone and （S）-（--）-citronellal. The key steps involved diastereoselective construction of two chiral carbon centers through the intramolecular chiral induction and uncommon Julia olefination of ketone forming the E-trisubstituted C（22）--C（23） double bound.展开更多
Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, ...Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.展开更多
基金Project supported by the National Natural Science Foundation of China （Nos. 20021001, 203900501） and the Chang Jiang Scholars Program of China.
文摘The stereocontrolled synthesis of the C（17）--C（28） fragment 3 of didemnaketal B was accomplished in 21 steps from the natural （R）-（＋）-pulegone and （S）-（--）-citronellal. The key steps involved diastereoselective construction of two chiral carbon centers through the intramolecular chiral induction and uncommon Julia olefination of ketone forming the E-trisubstituted C（22）--C（23） double bound.
基金Project supported by the National Natural Science Foundation of Chinathe State Key Laboratory of Bio-organicNatural Products Chemistry
文摘Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.
