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A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide.

ABSTRACT: Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established ¹³ C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.

SUBMITTER: Andringa RLH

PROVIDER: S-EPMC8362178 | biostudies-literature |

REPOSITORIES: biostudies-literature

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A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide.

Project description:A unified approach for the construction of the potent marine antitumor agents (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (+)-13-deoxytedanolide (2).

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