phomactin-a and oxadecalin

phomactin-a has been researched along with oxadecalin* in 2 studies

Other Studies

2 other study(ies) available for phomactin-a and oxadecalin

Article	Year
Construction of the tricyclic furanochroman skeleton of phomactin A via the Prins/Conia-ene cascade cyclization approach. The Journal of organic chemistry, 2011, Aug-19, Volume: 76, Issue:16 A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf)(3) in CH(3)CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps. Topics: Catalysis; Chromans; Cyclization; Epoxy Compounds; Furans; Heterocyclic Compounds, 4 or More Rings; Molecular Structure; Naphthalenes; Stereoisomerism	2011
Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction. Organic letters, 2001, Sep-20, Volume: 3, Issue:19 Phomactin A (1) is a selective antagonist of platelet activating factor (PAF). Herein, we report our progress toward the construction of the oxadecalin core of 1. This route is based on the Diels-Alder cycloaddition of an appropriately functionalized vinyl pyran and a complementary dienophile. A model of this reaction involving 2 and maleic anhydride was conducted. Adduct 3 contains the correct stereochemical arrangements between functional groups necessary for gaining access to phomactin A. Reaction: see text. Topics: Fungi; Heterocyclic Compounds, 4 or More Rings; Maleic Anhydrides; Models, Chemical; Naphthalenes; Platelet Activating Factor; Platelet Aggregation Inhibitors; Stereoisomerism	2001

Article

Year

Construction of the tricyclic furanochroman skeleton of phomactin A via the Prins/Conia-ene cascade cyclization approach.

The Journal of organic chemistry, 2011, Aug-19, Volume: 76, Issue:16

A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf)(3) in CH(3)CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps.

Topics: Catalysis; Chromans; Cyclization; Epoxy Compounds; Furans; Heterocyclic Compounds, 4 or More Rings; Molecular Structure; Naphthalenes; Stereoisomerism

2011

Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction.

Organic letters, 2001, Sep-20, Volume: 3, Issue:19

Phomactin A (1) is a selective antagonist of platelet activating factor (PAF). Herein, we report our progress toward the construction of the oxadecalin core of 1. This route is based on the Diels-Alder cycloaddition of an appropriately functionalized vinyl pyran and a complementary dienophile. A model of this reaction involving 2 and maleic anhydride was conducted. Adduct 3 contains the correct stereochemical arrangements between functional groups necessary for gaining access to phomactin A. Reaction: see text.

Topics: Fungi; Heterocyclic Compounds, 4 or More Rings; Maleic Anhydrides; Models, Chemical; Naphthalenes; Platelet Activating Factor; Platelet Aggregation Inhibitors; Stereoisomerism

2001