Total Synthesis of Jerangolid A
The first total synthesis of the antifungal polyketide jerangolid A has been accomplished. Starting with the readily available (R)-Roche ester and (S)-glycidol as chirons, the synthesis involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization for the construction of the dihydropy...
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| Veröffentlicht in: | Organic letters 2010-07, Vol.12 (14), p.3172-3175 |
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| creator | Hanessian, Stephen Focken, Thilo Oza, Rupal |
| description | The first total synthesis of the antifungal polyketide jerangolid A has been accomplished. Starting with the readily available (R)-Roche ester and (S)-glycidol as chirons, the synthesis involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization for the construction of the dihydropyran subunit. The lactone segment was built through a tandem NaOMe conjugate addition-lactonization reaction, and further functionalized through a sequence consisting of iodination, I−Mg exchange, and hydroxymethylation. Other key steps in the synthesis featured a novel application of a phosphonamide-anion based olefination and a Julia−Kocienski reaction. |
| doi_str_mv | 10.1021/ol101103q |
| format | Article |
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Starting with the readily available (R)-Roche ester and (S)-glycidol as chirons, the synthesis involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization for the construction of the dihydropyran subunit. The lactone segment was built through a tandem NaOMe conjugate addition-lactonization reaction, and further functionalized through a sequence consisting of iodination, I−Mg exchange, and hydroxymethylation. 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| ispartof | Organic letters, 2010-07, Vol.12 (14), p.3172-3175 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Biological Products - chemical synthesis Biological Products - chemistry Catalysis Pyrans - chemical synthesis Pyrans - chemistry Stereoisomerism |
| title | Total Synthesis of Jerangolid A |
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