Studies directed towards the total synthesis of narbonolide: stereoselective synthesis of the C1–C15 chain

Yadav, J. S.; Kavita, Aala; Rao, K. Nageswara; Mohapatra, Debendra K.

doi:10.1016/j.tetlet.2013.04.023

Cited by 1 publication

(2 citation statements)

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“…It is a 14-membered macrolactone belonging to the pikromycin family of antibiotics and was synthesized by desymmetrization, Evans aldol reaction, Takai olefination and Yamaguchi esterification as key steps. [36] The synthesis commenced from compound 4 which was converted into triol 262. The triol was converted into acid 263 in a series of steps.…”

Section: Narbonolidementioning

confidence: 99%

“…demonstrated a stereoselective synthesis of the C1−C15 chain of narbonolide. It is a 14‐membered macrolactone belonging to the pikromycin family of antibiotics and was synthesized by desymmetrization, Evans aldol reaction, Takai olefination and Yamaguchi esterification as key steps [36] . The synthesis commenced from compound 4 which was converted into triol 262 .…”

Section: Introductionmentioning

confidence: 99%

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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: Narbonolidementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%