Total Synthesis of (+)‐Bourgeanic Acid Utilizing Desymmetrization Strategy

Yadav, J. S.; Rao, K. Nageswara; Kontham, Ravindar; Reddy, B. V. Subba

doi:10.1002/ejoc.201001199

Cited by 21 publications

(3 citation statements)

References 24 publications

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“…The Yamaguchi esterification was employed in the preparation of large ring lactones from the corresponding open‐chain hydroxy acids (seco‐acids)17. As then, this esterification has found tremendous applications in the preparation of depsibonds on resin18, macrolactonization of seco‐acid peptides14, 18–20 and seco‐acid non peptides21–23.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of a depsidomycin analogue by convergent solid‐phase peptide synthesis and macrolactonization strategy for antitubercular activity

Venugopala

Alberício

Coovadia

et al. 2011

Journal of Peptide Science

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Depsidomycin is a cyclic heptadepsi-peptide isolated from the cultured broth of Streptomyces lavendofoliae MI951-62F2. It exhibits significant antimicrobial and immunosuppressive activity. The total synthesis of a depsidomycin analogue in which 1,2-piperazine-3-carboxylic acid was substituted with proline is described. After several trials using different strategies, the desired depsidomycin analogue was obtained via stepwise synthesis starting by the amino acid 'head' and macrolactonization under Yamaguchi conditions. The cyclic depsipeptide was evaluated to have an minimum inhibitory concentration (MIC) of 4 µg/ml against H37RV and 16 µg/ml against MDR clinical strains of MTB (MDR-MTB), while the linear precursor 8 also had MICs of 4 and 16 µg/ml for the susceptible and resistant strains, respectively.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of a depsidomycin analogue by convergent solid‐phase peptide synthesis and macrolactonization strategy for antitubercular activity

Venugopala

Alberício

Coovadia

et al. 2011

Journal of Peptide Science

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“…In 2011, our group accomplished a stereoselective synthesis of despide (+)-bourgeanic acid using desymmetrization of bicyclic olefin, Gillman's reaction, TEMPO oxidation of 1,3diol, and Yamaguchi lactonization as key steps. [29] Accordingly, the synthesis commenced from bicyclic lactone 8 a which upon reduction with LiAlH 4 provided the triol 210 in 83 % yield. The diol 211 was obtained from triol 210 by a series of steps.…”

Section: (+)-Bourgeanic Acidmentioning

confidence: 99%

Desymmetrisation of meso‐2,4‐Dimethyl‐8‐oxabicyclo[3.2.1]‐oct‐6‐ene‐3‐ol and its Application in Natural Product Syntheses

Tadiparthi

Anand

Sakirolla

et al. 2021

The Chemical Record

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The compounds containing chiral centers and different functional groups serve as magnificent building blocks for the preparation of various natural products that are having immense biological activity. “Dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol” is one of the wonderful synthons to construct multiple stereo centers at a time during the asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various simple and complex natural products from the past three decades (1995–2020) by using dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol as a synthon. Moreover, the synthetic utility of this starting material was investigated and well demonstrated. Further, we executed the desymmetrization of dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol by hydroboration to get different chiral centers. After obtaining the stereocenters, we could manage either the fragment, formal or total synthesis of natural products, by simple protection and deprotection sequence followed by C−C bond formation steps.

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“…Furthermore, other methods for the stereoselective assembly of long sequences of stereocenters in polypropionates have been developed. These methods include crotylations [ 10 , 11 , 12 ], allenylations [ 13 , 14 , 15 ], selective radical processes [ 16 , 17 , 18 , 19 ], sequential substitutions [ 20 , 21 ], epoxide ring openings [ 22 , 23 , 24 , 25 ], Diels–Alder [ 26 ], and others [ 27 , 28 , 29 , 30 ] ( Figure 3 ).…”

Section: Introductionmentioning

confidence: 99%

Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products

Rodríguez-Berríos

Isbel

Bugarin

2023

IJMS

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Polypropionate units are a common structural feature of many of the natural products in polyketides, some of which have shown a broad range of antimicrobial and therapeutic potential. Polypropionates are composed of a carbon skeleton with alternating methyl and hydroxy groups with a specific configuration. Different approaches have been developed for the synthesis of polypropionates and herein we include, for the first time, all of the epoxide-based methodologies that have been reported over the years by several research groups such as Kishi, Katsuki, Marashall, Miyashita, Prieto, Sarabia, Jung, McDonald, etc. Several syntheses of polypropionate fragments and natural products that employed epoxides as key intermediates have been described and summarized in this review. These synthetic approaches involve enatio- and diastereoselective synthesis of epoxides (epoxy-alcohols, epoxy-amides, and epoxy-esters) and their regioselective cleavage with carbon and/or hydride nucleophiles. In addition, we included a description of the isolation and biological activities of the polypropionates and related natural products that have been synthetized using epoxide-based approaches. In conclusion, the epoxide-based methodologies are a non-aldol alternative approach for the construction of polypropionate.

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Total Synthesis of (+)‐Bourgeanic Acid Utilizing Desymmetrization Strategy

Cited by 21 publications

References 24 publications

Total synthesis of a depsidomycin analogue by convergent solid‐phase peptide synthesis and macrolactonization strategy for antitubercular activity

Total synthesis of a depsidomycin analogue by convergent solid‐phase peptide synthesis and macrolactonization strategy for antitubercular activity

Desymmetrisation of meso‐2,4‐Dimethyl‐8‐oxabicyclo[3.2.1]‐oct‐6‐ene‐3‐ol and its Application in Natural Product Syntheses

Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products

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