Four-Step Total Synthesis of (+)-Yaoshanenolides A and B | Zendy

Sagar S. Thorat | Zendy; Megha N. Palange | Zendy; Ravindar Kontham | Zendy

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Four-Step Total Synthesis of (+)-Yaoshanenolides A and B

Author(s) -

Sagar S. Thorat,

Megha N. Palange,

Ravindar Kontham

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b00701

Subject(s) - furan , total synthesis , chemistry , aldol reaction , yield (engineering) , cycloaddition , lactone , aldehyde , stereochemistry , derivative (finance) , aldol condensation , combinatorial chemistry , organic chemistry , catalysis , materials science , economics , financial economics , metallurgy

A highly concise bioinspired four-step total synthesis of yaoshanenolides A and B possessing tricyclic spirolactone with an unusual 5' H -spiro-[bicyclo[2.2.2]-oct[2]ene-7,2'-furan]-5'-one scaffold is reported. This synthesis features high-yielding aldol-type addition of γ-butyrolactone on to the aldehyde, exocyclic olefination of lactone derivative using Eschenmoser's salt, and highly facial- and endo-selective [4 + 2]-cycloaddition of fully functionalized 5-methylene-2(5 H )-furanone with natural R -(-)-α-phellandrene. The approach allows access to yaoshanenolides A and B in four linear steps in 11 and 13% overall yield.

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