2016
DOI: 10.1002/ejoc.201601172
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Total Enantioselective Synthesis of the Endophytic Fungal Polyketide Phomolide H and Its Structural Revision

Abstract: A total synthesis of the proposed structure of the natural polyketide‐macrolactone phomolide H 2 has been achieved following a bidirectional strategy from l‐tartaric acid. The originally assigned structure of phomolide H displayed discordant NMR spectroscopic data in comparison with synthetic 2. The synthetic strategy was extended to prepare diastereomers and epimeric methyl‐ethers of the natural product, structural analysis of which revealed a match of the natural product with diastereomer 27. The structural … Show more

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Cited by 8 publications
(5 citation statements)
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“…The crude product was purified by column chromatography (hexane/EtOAc 9:1) to afford the chiral auxiliary 5b (1.70 g) as a bright yellow oil in a 90% yield. All spectroscopic and physical data were in agreement with those reported in the literature [ 37 ]. R f = 0.23 (hexanes/EtOAc 9:1 KMnO 4 stain); 1 H NMR (400 MHz, CDCl 3 ) δ 5.14 (ddd, J = 7.7, 6.1, 1.2 Hz, 1H), 3.50 (dd, J = 11.5, 8.1 Hz, 1H), 3.01 (dd, J = 11.5, 1.2 Hz, 1H), 2.76 (s, 3H), 2.41–2.31 (m, 1H), 1.05 (d, J = 6.8 Hz, 3H), 0.96 (d, J = 7.0 Hz, 3H).…”
Section: Methodssupporting
confidence: 88%
“…The crude product was purified by column chromatography (hexane/EtOAc 9:1) to afford the chiral auxiliary 5b (1.70 g) as a bright yellow oil in a 90% yield. All spectroscopic and physical data were in agreement with those reported in the literature [ 37 ]. R f = 0.23 (hexanes/EtOAc 9:1 KMnO 4 stain); 1 H NMR (400 MHz, CDCl 3 ) δ 5.14 (ddd, J = 7.7, 6.1, 1.2 Hz, 1H), 3.50 (dd, J = 11.5, 8.1 Hz, 1H), 3.01 (dd, J = 11.5, 1.2 Hz, 1H), 2.76 (s, 3H), 2.41–2.31 (m, 1H), 1.05 (d, J = 6.8 Hz, 3H), 0.96 (d, J = 7.0 Hz, 3H).…”
Section: Methodssupporting
confidence: 88%
“…14). 94 On the other hand, the signicant deviation between the reported quasi-molecular ion peak at m/z 281.1532 ([M + Na] + ) and the calculated value (281.1365) suggested a different formula.…”
Section: Functional Group Misidenticationmentioning
confidence: 94%
“…18 It is notable that stagochromene A isolated along with stagonolides A, J, and K from S. cirsii 15 has a similar skeleton and can also be a congener of TMLs. Natural product 21 as well as phomolides D-H (22)(23)(24)(25)(26) were isolated from different endophytic strains of Phomopsis sp. Compound 21 showed phytotoxic activity on germination and radicle growth of Medicago sativa, Trifolium hybridum, and Buchloe dactyloides with IC 50 values for germination 15.8, 24.2, and 31.2 mg mL −1 , and for radicle growth 31.9, 63.3, 130.9 mg mL −1 , respectively.…”
Section: Reviewmentioning
confidence: 99%
“…Compound 21 showed phytotoxic activity on germination and radicle growth of Medicago sativa, Trifolium hybridum, and Buchloe dactyloides with IC 50 values for germination 15.8, 24.2, and 31.2 mg mL −1 , and for radicle growth 31.9, 63.3, 130.9 mg mL −1 , respectively. 19 Phomolides D-H (22)(23)(24)(25)(26) had no effects on the growth of E. coli, B. subtilis, B. pumilus, S. aureus, and C. albicans at 30 mg per plate using the Oxford plate assay system. 20 The absolute congurations of phomolides G and H were revised by , and McNulty and McLeod (2017) using enantioselective total synthesis (Fig.…”
Section: Reviewmentioning
confidence: 99%