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Synfacts 2022; 18(01): 0001
DOI: 10.1055/s-0041-1737183
Synthesis of Natural Products and Potential Drugs

Synthesis of (+)-Cyclobutastellettolide B

Contributor(s):
Erick M. Carreira
,
Lukas Lüthy
Zhang Z, Chen S, Tang F, Guo K, Liang X.-T, Huang J, *, Yang Z. * Peking University Shenzhen Graduate School, P. R. of China
Total Synthesis of (+)-Cyclobutastellettolide B.

J. Am. Chem. Soc. 2021;
143: 18287-18293
DOI: 10.1021/jacs.1c08880.
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Key words

(+)-cyclobutastellettolide B - Johnson–Claisen rearrangement - Simmons–Smith cyclopropanation - Norrish–Yang cyclization

Significance

(+)-Cyclobutastellettolide B is a natural product isolated in 2019 from a Stelleta sp. sponge (S. A. Kolesnikova et al. J. Nat. Prod. 2019, 82, 3196). It features a 6/6/4 fused tricyclic core, including a fully substituted cyclobutane, rendering it an interesting target for total synthesis.


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Comment

Vinyl bromide B was rapidly elaborated into ester D using a Johnson–Claisen rearrangement. Installation of the α-tertiary aldehyde in H was achieved via ring opening of the cyclopropane in G. Wittig reaction followed by oxidation yielded diketone J which smoothly underwent the desired Norrish–Yang cyclization, followed by lactonization, to yield the natural product.


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Publication History

Article published online:
17 December 2021

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