Application of fluorous methodologies for the total synthesis of eight diastereomers of passifloricin A and 6-epi-dictyostatin. Gustavo Moura-Letts

ISBN: 9780549732488

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248 pages


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Application of fluorous methodologies for the total synthesis of eight diastereomers of passifloricin A and 6-epi-dictyostatin.  by  Gustavo Moura-Letts

Application of fluorous methodologies for the total synthesis of eight diastereomers of passifloricin A and 6-epi-dictyostatin. by Gustavo Moura-Letts
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A soluble fluorous palladacycle complex that promotes the Heck coupling and can be recovered and reused is reported herein. This complex promoted the Heck coupling of acrylates and haloarenes in high yields and with high turnoverMoreA soluble fluorous palladacycle complex that promotes the Heck coupling and can be recovered and reused is reported herein. This complex promoted the Heck coupling of acrylates and haloarenes in high yields and with high turnover numbers.-Passifloricin A, a natural product isolated from the tree Passiflora foetida is a polyol-lactone containing four stereocenters.

The fluorous mixture synthesis (FMS) of all eight diastereomers of passifloricin A is reported herein. Utilizing a multiple-tag FMS strategy we successfully obtained the eight quasiisomers from the natural product. The spectroscopic data for synthetic passifloricin A matched the spectroscopic data for natural passifloricin A.-The ene-diene cross-metathesis reaction was succesfully applied to a wide variety of enes and dienes in high yields and streoselectivities.

This reaction was applied for the synthesis of 10 grams of the bottom fragment of dictyostatin.-Dictyostatin, a marine sponge-derived macrolactone has been extensively studied in the Curran group because of its high potency as a microtubule-stabilizing agent. Based on SAR studies it was synthesized the 6-epimer (four times more potent). We successfully coupled the fragments via dimethylsilaketal formation and ring closing metathesis reaction of the silaketal intermediate. The final steps led to the synthesis of 30 mg of 6-epi-dictyostatin for the testing of its antiploriferative activity in vivo.



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