Total synthesis and structural elucidation of spongosoritin A

Lisa J. Alcock; Matthew D. Norris; Michael V. Perkins

doi:10.1039/c7ob03150e

Total synthesis and structural elucidation of spongosoritin A

College of Science and Engineering

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

3 Citations (Scopus)

Abstract

Two putative structures of spongosoritin A, with syn (6R,8R) and anti (6S,8R) configurations, were each synthesised in a total of 11 linear steps with only 8 purification procedures. The key steps in our strategy included Evans alkylation and olefin dihydroxylation to install the C8 and C6 stereocentres, a transacetalisation/dehydration cascade to construct the furanylidene core, and chromatographic separation of 9E- and 9Z-isomers of the final compounds with silver nitrate impregnated silica. Comparison of the ¹H and ¹³C NMR data for the synthetic syn- and anti-isomers to that reported for the natural product revealed that the relative configuration of spongosoritin A is syn. The absolute stereochemistry was also confirmed as 6R,8R based on optical rotation measurements where the synthetic syn (6R,8R) and natural product had the same sign of optical rotation (negative).

Original language	English
Pages (from-to)	1351-1358
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	8
Early online date	29 Jan 2018
DOIs	https://doi.org/10.1039/c7ob03150e
Publication status	Published - 28 Feb 2018

Bibliographical note

Funding Information:
We wish to thank Flinders University for funding, support and facilities. LJA acknowledges receipt of the Ferry Honours Scholarship and MDN acknowledges receipt of the MF & MH Joyner PhD Scholarship in Science.

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

Keywords

spongosoritin A
Marine sponges

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title = "Total synthesis and structural elucidation of spongosoritin A",

abstract = "Two putative structures of spongosoritin A, with syn (6R,8R) and anti (6S,8R) configurations, were each synthesised in a total of 11 linear steps with only 8 purification procedures. The key steps in our strategy included Evans alkylation and olefin dihydroxylation to install the C8 and C6 stereocentres, a transacetalisation/dehydration cascade to construct the furanylidene core, and chromatographic separation of 9E- and 9Z-isomers of the final compounds with silver nitrate impregnated silica. Comparison of the 1H and 13C NMR data for the synthetic syn- and anti-isomers to that reported for the natural product revealed that the relative configuration of spongosoritin A is syn. The absolute stereochemistry was also confirmed as 6R,8R based on optical rotation measurements where the synthetic syn (6R,8R) and natural product had the same sign of optical rotation (negative).",

keywords = "spongosoritin A, Marine sponges",

author = "Alcock, \{Lisa J.\} and Norris, \{Matthew D.\} and Perkins, \{Michael V.\}",

note = "Funding Information: We wish to thank Flinders University for funding, support and facilities. LJA acknowledges receipt of the Ferry Honours Scholarship and MDN acknowledges receipt of the MF \& MH Joyner PhD Scholarship in Science. Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

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AU - Alcock, Lisa J.

AU - Norris, Matthew D.

AU - Perkins, Michael V.

N1 - Funding Information: We wish to thank Flinders University for funding, support and facilities. LJA acknowledges receipt of the Ferry Honours Scholarship and MDN acknowledges receipt of the MF & MH Joyner PhD Scholarship in Science. Publisher Copyright: © 2018 The Royal Society of Chemistry.

PY - 2018/2/28

Y1 - 2018/2/28

N2 - Two putative structures of spongosoritin A, with syn (6R,8R) and anti (6S,8R) configurations, were each synthesised in a total of 11 linear steps with only 8 purification procedures. The key steps in our strategy included Evans alkylation and olefin dihydroxylation to install the C8 and C6 stereocentres, a transacetalisation/dehydration cascade to construct the furanylidene core, and chromatographic separation of 9E- and 9Z-isomers of the final compounds with silver nitrate impregnated silica. Comparison of the 1H and 13C NMR data for the synthetic syn- and anti-isomers to that reported for the natural product revealed that the relative configuration of spongosoritin A is syn. The absolute stereochemistry was also confirmed as 6R,8R based on optical rotation measurements where the synthetic syn (6R,8R) and natural product had the same sign of optical rotation (negative).

AB - Two putative structures of spongosoritin A, with syn (6R,8R) and anti (6S,8R) configurations, were each synthesised in a total of 11 linear steps with only 8 purification procedures. The key steps in our strategy included Evans alkylation and olefin dihydroxylation to install the C8 and C6 stereocentres, a transacetalisation/dehydration cascade to construct the furanylidene core, and chromatographic separation of 9E- and 9Z-isomers of the final compounds with silver nitrate impregnated silica. Comparison of the 1H and 13C NMR data for the synthetic syn- and anti-isomers to that reported for the natural product revealed that the relative configuration of spongosoritin A is syn. The absolute stereochemistry was also confirmed as 6R,8R based on optical rotation measurements where the synthetic syn (6R,8R) and natural product had the same sign of optical rotation (negative).

KW - spongosoritin A

KW - Marine sponges

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DO - 10.1039/c7ob03150e

M3 - Article

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AN - SCOPUS:85042675958

SN - 1477-0520

VL - 16

SP - 1351

EP - 1358

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 8

ER -

Total synthesis and structural elucidation of spongosoritin A

Abstract

Bibliographical note

Keywords

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