A highly convergent and concise total syntheses of (3R,5R)-Sonnerlactone and (3R,5S) Sonnerlactone from a readily available L-malic acid is described. The following series of reactions such as Barbier allylation, photochemical esterification and Ring Closing Metathesis (RCM) are utilized as key steps to accomplish their syntheses.
LiK-K, LuY-J, SongX-H, SheZ-G, WuX-W, AnL-K, YeC-X, LinY-C. (2010) The metabolites of Mangrove endophytic fungus Zh6-B1 from the South China Sea. Bioorganic and Medicinal Chemistry Letters, 20, 3326–3328.
2.
Rivero-CruzJF, Garcia-AguirreG, Cerda-Garcia-RojasCM, MataR. (2000) Conformational behavior and absolute stereostructure of two phytotoxic nonenolides from the fungus Phoma herbarum. Tetrahedron, 56, 5337–5344
3.
Rivero-CruzJF, MaciasM, Cerda- Garcia-RojasCM, MataR. (2003) A new phytotoxic nonenolide from Phoma herbarum. Journal of Natural Products, 66, 511–514.
4.
EdradaRA, HeubesM, BrauersG, WrayV, BergA, GrafeU, WohlfarthM, MuhlbacherJ, SchaumannK, SudarsonoS, BringmannG, ProkschP. (2002) Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua. Journal of Natural Products, 65, 1598–1604.
5.
EvidenteA, CimminoA, BerestetskiyA, MitinaG, AndolfiA, MottaA. (2008) Stagonolides B-F, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide of Cirsiumarvense. Journal of Natural Products, 71, 31–34
6.
GreveH, SchuppPJ, EguerevaE, KehrausS, KonigGM. (2008) Ten-membered lactones from the marine-derived fungus, Curvularia sp. Journal of Natural Products, 71, 1651–1653.
7.
YadavJS, ShankarKS, ReddyAS, ReddyBVS. (2012) The stereoselective total synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone. Tetrahedron Letters, 53, 6380–6382
8.
ThirupathiB, GundapaneniRR, MohapatraDK. (2011) First total syntheses of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone. Synlett, 18, 2667–2670
9.
SanaboinaC, ChidaraS, JanaS, EppakayalaL. (2016) Total synthesis of (3R,5R) and (3R,5S)-sonnerlactones. Tetrahedron Letters, 57, 1767–1770.
10.
HanessianS, UgoliniA, DubeD, GlamyanA. (1984) Facile access to (S)-1,2,4-butanetriol and its derivatives. Canadian Journal of Chemistry, 62, 2146–2147
PetrierC, LucheJL. (1985) Allylzinc reagents additions in aqueous media. Journal of Organic Chemistry, 50, 910–912
13.
LucheJL, EinhornCJ. (1987) Selective allylation of carbonyl compounds in aqueous media. Journal of Organometallic Chemistry, 322, 177–183
14.
SharmaG V M, KumarRK. (2004) Studies directed towards the total synthesis of feigrisolide B. Tetrahedron Asymmetry, 15, 2323–2326.
15.
YadavJS, RaoYG, RavindarK, ReddyBVS, NarsaiahAV. (2009) Total synthesis of xestodecalactone C from L-malic acid. Synthesis, 3157–3161.
16.
KrishnaPR, SrinivasR. (2008) The first synthesis of a 12-membered macrolide natural product via a RCM protocol: Determination of absolute stereochemistry. Tetrahedron Asymmetry, 19, 1153–1160.
17.
BajwaN, JenningsMP. (2008) Syntheses of epi-aigialomycin D and deoxy-aigialomycin C via a diastereoselective ring closing metathesis macrocyclization Protocol. Tetrahedron Letters, 49, 390–393.
18.
FortanetJG, DeberghJR, De BrabanderJK. (2005) A photochemical entry to depsides: synthesis of gustastatin. Organic Letters, 7, 685–688
19.
SoltaniO, De BrabanderJK. (2005) Synthesis of functionalized salicylate esters and amides by photochemical acylation. Angewandte Chemie International Edition, 44, 1696–1699
20.
HubenK, ZhuZ, BallyT, GebickiJ. (1997) X-ray-induced transformation of o-vinylbenzaldehyde and 2-methylbenzocyclobutenone to an o-quinoid ketene and its radical cation. Journal of the American Chemical Society, 119, 2825–2831
21.
GündüzH, KumbaraciV, TalinliN. (2014) Reactions of quino-ketenes with C-nucleophiles: syntheses of (2-hydroxyphenyl)methanols and 2-hydroxyphenyl ketones. Helvetica Chimica Acta, 97, 1097–1106.
22.
SchollM, DingS, LeeCW, GrubbsRH. (1999) Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands. Organic Letters, 1, 953–956
23.
BajwaN, JenningsMP. (2008) Synthesis and activity of a new generation of Ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Tetrahedron Letters, 49, 390–393.
Supplementary Material
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
