Application of desymmetrization protocol for the formal total synthesis of emericellamide B

Mohapatra, Debendra K.; Hossain, Sk. Samad; Dhara, Santu; Yadav, J. S.

doi:10.1016/j.tetlet.2010.04.015

Cited by 10 publications

(4 citation statements)

References 21 publications

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“…In 2010, Yadav et al executed the synthesis of emericellamide B by using the desymmetrization technique as a key step. [25] Initially, the bicyclic lactone 8 b was converted into triol 24 and was further converted into diol 168 in three steps. The primary hydroxyl group in 168 was protected as TBS ether, followed by esterification with BocÀ AlaÀ OH and subsequent desilylation with CSA gave 169 in 56 % yield over three steps.…”

Section: Emericellamide Bmentioning

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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Section: Emericellamide Bmentioning

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 latter, after several steps, gave the target product emericellamide B 199 (Scheme 36). [226] In the following, Wei and co-workers in 2015 achieved and reported total synthesis of emericellamide B. [229] Asymmetric total synthesis of emericellamide B was accomplished in 17 longest linear steps with 9.4% yields.…”

Section: -Membered Macrolidesmentioning

confidence: 99%

“…A convergent formal total synthesis of emericellam Yadavide B, a 19-membered antibacterial depsipeptide was demonstrated by Yadav and co-workers in 2010. [226] The key aspect of the…”

Section: -Membered Macrolidesmentioning

confidence: 99%

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

et al. 2020

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The Wittig reaction involves the synthesis of an alkene via the conversion of an aldehyde or ketone with the already generated ylide from a phosphonium salt. Significantly, when this important name reaction is employed the desired alkenes are constructed via a predictable manner, thus resultant particularly are useful in the total synthesis of natural products and synthetic complex organic compounds with definite geometric isomers, exhibiting diverse biological potencies. In this review we try to highlight the applications of the Wittig reaction as an efficient and attractive strategy in the total synthesis of macrolides from 2008 to 2020.

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“…5 Ghosh et al further explored a Paterson anti-aldol reaction, 6 and Yaday et al utilized the desymmetrization of a bicyclic precursor to generate the polyketide building block. 7 A common feature of all these syntheses is a long linear sequence of at least 10 steps for generating a suitable synthetic building block for the ongoing synthesis.…”

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confidence: 99%

A Straightforward Synthesis of Emericellamide A Using Matteson’s Homologation Approach

Priester

Kazmaier

2023

Synlett

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Application of desymmetrization protocol for the formal total synthesis of emericellamide B

Cited by 10 publications

References 21 publications

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

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

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

A Straightforward Synthesis of Emericellamide A Using Matteson’s Homologation Approach

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