Das, Dipendu ; Kant, Ruchir ; Chakraborty, Tushar Kanti (2014) An Approach to a Bislactone Skeleton: A Scalable Total Synthesis of (±)-Penifulvin A Organic Letters, 16 (10). pp. 2618-2621. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/ol500768w
Related URL: http://dx.doi.org/10.1021/ol500768w
Abstract
An efficient and scalable total synthesis of the architecturally challenging sesquiterpenoid (±)-penifulvin A has been accomplished via a 12-step sequence with an overall yield of 16%. For the construction of this structurally complex tetracyclic molecule, the key steps used included 1,4-conjugate addition, a Pd(0) catalyzed cross-coupling reaction between an enol phosphate and trimethyl aluminum, Claisen rearrangement using the Johnson orthoester protocol, Ti(III)-mediated reductive epoxide opening–cyclization, Lewis acid catalyzed epoxy-aldehyde rearrangement, and finally a substrate controlled oxidative cascade lactonization process.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 131111 |
| Deposited On: | 02 Dec 2022 10:59 |
| Last Modified: | 02 Dec 2022 10:59 |
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