Total synthesis of altissimacoumarin D, a small molecule sirtuin1 activator

Anna C. Silva; Hanae Benelkebir; Rosangela S. C. Lopes; Claudio C. Lopes; A. Ganesan

doi:10.21577/0103-5053.20180021

Total synthesis of altissimacoumarin D, a small molecule sirtuin1 activator

Anna C. Silva
, Hanae Benelkebir
, Rosangela S. C. Lopes
, Claudio C. Lopes
, A. Ganesan

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

28 Downloads (Pure)

Abstract

The total synthesis of the plant natural product altissimacoumarin D was achieved by the Mitsunobu alkylation of isofraxidin by geraniol. Isofraxidin was prepared from 2,4-dihydroxybenzaldehyde in five steps. The key reaction was the Knoevenagel condensation of an ortho-hydroxybenzaldehyde with Meldrum’s acid under neutral conditions in water and one-pot acid catalyzed cyclization to the coumarin.

Original language	English
Pages (from-to)	1157-1161
Number of pages	5
Journal	Journal of the Brazilian Chemical Society
Volume	29
Issue number	5
DOIs	https://doi.org/10.21577/0103-5053.20180021
Publication status	Published - 9 Feb 2018

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Cite this

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title = "Total synthesis of altissimacoumarin D, a small molecule sirtuin1 activator",

abstract = "The total synthesis of the plant natural product altissimacoumarin D was achieved by the Mitsunobu alkylation of isofraxidin by geraniol. Isofraxidin was prepared from 2,4-dihydroxybenzaldehyde in five steps. The key reaction was the Knoevenagel condensation of an ortho-hydroxybenzaldehyde with Meldrum{\textquoteright}s acid under neutral conditions in water and one-pot acid catalyzed cyclization to the coumarin.",

author = "Silva, \{Anna C.\} and Hanae Benelkebir and Lopes, \{Rosangela S. C.\} and Lopes, \{Claudio C.\} and A. Ganesan",

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AU - Silva, Anna C.

AU - Benelkebir, Hanae

AU - Lopes, Rosangela S. C.

AU - Lopes, Claudio C.

AU - Ganesan, A.

PY - 2018/2/9

Y1 - 2018/2/9

N2 - The total synthesis of the plant natural product altissimacoumarin D was achieved by the Mitsunobu alkylation of isofraxidin by geraniol. Isofraxidin was prepared from 2,4-dihydroxybenzaldehyde in five steps. The key reaction was the Knoevenagel condensation of an ortho-hydroxybenzaldehyde with Meldrum’s acid under neutral conditions in water and one-pot acid catalyzed cyclization to the coumarin.

AB - The total synthesis of the plant natural product altissimacoumarin D was achieved by the Mitsunobu alkylation of isofraxidin by geraniol. Isofraxidin was prepared from 2,4-dihydroxybenzaldehyde in five steps. The key reaction was the Knoevenagel condensation of an ortho-hydroxybenzaldehyde with Meldrum’s acid under neutral conditions in water and one-pot acid catalyzed cyclization to the coumarin.

U2 - 10.21577/0103-5053.20180021

DO - 10.21577/0103-5053.20180021

M3 - Article

SN - 0103-5053

VL - 29

SP - 1157

EP - 1161

JO - Journal of the Brazilian Chemical Society

JF - Journal of the Brazilian Chemical Society

IS - 5

ER -