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Diastereo- and Enantioselective Access to Stereotriads Through a Flexible Coupling of Substituted Aldehydes and Alkenes

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Specialty Chemistry
Date 2019 Mar 29
PMID 30919530
Citations 3
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Abstract

A flexible redox-neutral coupling of aldehydes and alkenes enables rapid access to stereotriads starting from a single stereocenter with perfect levels of enantio- and diastereoselectivity under mild conditions. The versatility of the method is highlighted by the installation of heteroatoms along the tether, which enables a route to structurally diverse building blocks. The formal synthesis of (+)-neopeltolide further demonstrates the synthetic utility of this approach.

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Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes.

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References
1.
Varela A, Garve L, Leonori D, Aggarwal V . Stereocontrolled Total Synthesis of (-)-Stemaphylline. Angew Chem Int Ed Engl. 2017; 56(8):2127-2131. PMC: 5484348. DOI: 10.1002/anie.201611273. View

2.
Bootwicha T, Feilner J, Myers E, Aggarwal V . Iterative assembly line synthesis of polypropionates with full stereocontrol. Nat Chem. 2017; 9(9):896-902. DOI: 10.1038/nchem.2757. View

3.
Mungkornasawakul P, Chaiyong S, Sastraruji T, Jatisatienr A, Jatisatienr C, Pyne S . Alkaloids from the roots of Stemona aphylla. J Nat Prod. 2009; 72(5):848-51. DOI: 10.1021/np900030y. View

4.
Lu L, Zhang W, Carter R . Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2. J Am Chem Soc. 2008; 130(23):7253-5. PMC: 2435505. DOI: 10.1021/ja803012n. View

5.
Bauer A, Maulide N . A Stereoselective Reductive Hosomi-Sakurai Reaction. Org Lett. 2018; 20(5):1461-1464. DOI: 10.1021/acs.orglett.8b00276. View