Unknown

Dataset Information

0

Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes.

ABSTRACT: We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11-16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations enable the synthesis of ent-pimaranes bearing different modifications in the A- and C-rings.

SUBMITTER: Plangger I 

PROVIDER: S-EPMC7613685 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Short, Divergent, and Enantioselective Total Synthesis of Bioactive <i>ent</i>-Pimaranes.

Plangger Immanuel I   Wurst Klaus K   Magauer Thomas T  

Organic letters 20220928 39

We present the first total synthesis of eight <i>ent</i>-pimaranes via a short and enantioselective route (11-16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations enable the synthesis of <i>ent</i>-pimaranes bearing different modifications in the A- and  ...[more]

Similar Datasets

Unknown Short, enantioselective total synthesis of chatancin.
| S-EPMC4300267 | biostudies-literature
Unknown Short, Enantioselective Total Synthesis of (+)-Ineleganolide.
| S-EPMC12703658 | biostudies-literature
Unknown Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.
| S-EPMC4972021 | biostudies-literature
Unknown Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin.
| S-EPMC6220842 | biostudies-literature
Unknown Asymmetric total synthesis of ent-cyclooroidin.
| S-EPMC3099645 | biostudies-literature
Unknown Total synthesis of (-)- and ent-(+)-vindoline.
| S-EPMC2587129 | biostudies-literature
Unknown Total synthesis of <i>ent</i>-pavettamine.
| S-EPMC8204129 | biostudies-literature
Unknown Total Synthesis of <i>ent</i>-Plagiochianin B.
| S-EPMC7901668 | biostudies-literature
Unknown Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis.
| S-EPMC5215435 | biostudies-literature
Unknown Enantioselective total synthesis of (+)-reserpine.
| S-EPMC3578295 | biostudies-literature