Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters

Sheenagh G Aiken; Dylan Rigby; Daniele Fiorito; Malcolm R P George; Simon Wübbolt; Adam Noble; Varinder K Aggarwal

doi:10.1002/anov.70003

Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters

Sheenagh G Aiken, Dylan Rigby, Daniele Fiorito, Malcolm R P George, Simon Wübbolt, Adam Noble, Varinder K Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

Abstract

Mycapolyol E is a cytotoxic PKS-NRPS metabolite isolated from a marine sponge containing an extended polyacetate motif, terminal formamide moiety and tetramic acid-derived headgroup, whose structure could not be fully elucidated upon isolation. A modular approach was employed and the ten 1,3-related hydroxy-substituted stereocenters were installed through iterative diboration/homologation reactions. Furthermore, the stereochemistry of the unassigned methyl stereocenter at C-5 was elucidated through partial synthesis and NMR analysis, and the uncertainty surrounding the relative stereochemistry of the 1,3-polyol was resolved. The stereochemistry and structure of mycapolyol E was confirmed through total synthesis, which was completed in 20 steps (LLS).

Original language	English
Article number	e70003
Number of pages	7
Journal	Angewandte Chemie Novit
Volume	1
Issue number	1
Early online date	25 Jul 2025
DOIs	https://doi.org/10.1002/anov.70003
Publication status	E-pub ahead of print - 25 Jul 2025

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Organic & Biological

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Synthesis and Structure Elucidation of Natural Products
Aggarwal, V. K. (Principal Investigator)
1/02/21 → 31/01/26
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title = "Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters",

abstract = "Mycapolyol E is a cytotoxic PKS-NRPS metabolite isolated from a marine sponge containing an extended polyacetate motif, terminal formamide moiety and tetramic acid-derived headgroup, whose structure could not be fully elucidated upon isolation. A modular approach was employed and the ten 1,3-related hydroxy-substituted stereocenters were installed through iterative diboration/homologation reactions. Furthermore, the stereochemistry of the unassigned methyl stereocenter at C-5 was elucidated through partial synthesis and NMR analysis, and the uncertainty surrounding the relative stereochemistry of the 1,3-polyol was resolved. The stereochemistry and structure of mycapolyol E was confirmed through total synthesis, which was completed in 20 steps (LLS). ",

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T1 - Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters

AU - Aiken, Sheenagh G

AU - Rigby, Dylan

AU - Fiorito, Daniele

AU - George, Malcolm R P

AU - Wübbolt, Simon

AU - Noble, Adam

AU - Aggarwal, Varinder K

PY - 2025/7/25

Y1 - 2025/7/25

N2 - Mycapolyol E is a cytotoxic PKS-NRPS metabolite isolated from a marine sponge containing an extended polyacetate motif, terminal formamide moiety and tetramic acid-derived headgroup, whose structure could not be fully elucidated upon isolation. A modular approach was employed and the ten 1,3-related hydroxy-substituted stereocenters were installed through iterative diboration/homologation reactions. Furthermore, the stereochemistry of the unassigned methyl stereocenter at C-5 was elucidated through partial synthesis and NMR analysis, and the uncertainty surrounding the relative stereochemistry of the 1,3-polyol was resolved. The stereochemistry and structure of mycapolyol E was confirmed through total synthesis, which was completed in 20 steps (LLS).

AB - Mycapolyol E is a cytotoxic PKS-NRPS metabolite isolated from a marine sponge containing an extended polyacetate motif, terminal formamide moiety and tetramic acid-derived headgroup, whose structure could not be fully elucidated upon isolation. A modular approach was employed and the ten 1,3-related hydroxy-substituted stereocenters were installed through iterative diboration/homologation reactions. Furthermore, the stereochemistry of the unassigned methyl stereocenter at C-5 was elucidated through partial synthesis and NMR analysis, and the uncertainty surrounding the relative stereochemistry of the 1,3-polyol was resolved. The stereochemistry and structure of mycapolyol E was confirmed through total synthesis, which was completed in 20 steps (LLS).

U2 - 10.1002/anov.70003

DO - 10.1002/anov.70003

M3 - Article (Academic Journal)

SN - 2510-9537

VL - 1

JO - Angewandte Chemie Novit

JF - Angewandte Chemie Novit

IS - 1

M1 - e70003

ER -

Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters

Abstract

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