Total Synthesis of (+)-Fusarisetin A Driven by a One-Pot Four-Reaction Process

Liu, Chenguang; Zeng, Zhixiong; Chen, Renzhi; Jiang, Xunjin; Wang, Yinglu; Zhang, Yandong

doi:10.1021/acs.orglett.6b00036

Cited by 19 publications

(9 citation statements)

References 55 publications

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“…The combined organic layers were washed with brine and dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was purified by flash chromatography on silica gel (20% EtOAc/Hexane) to give the dienol 5 as a colorless oil (1.12 g, 92 %); [α]D 23 +12.9 (c 1.00, CHCl3); (R)-4,8-Dimethylnon-7-en-1-yne (9). Method A: (R)-Citronellal 8 (1.00 g, 6.48 mmol) was added to a mixture of diethyl (1-diazo-2-oxopropyl)phosphonate (1.87 g, 9.72 mmol) and K2CO3 (1.79 g, 13.0 mmol) in methanol (15 mL).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Allahabadolactone A

Wang

Bates

2017

J. Org. Chem.

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A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Allahabadolactone A

Wang

Bates

2017

J. Org. Chem.

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“…In analogy to ref , to a solution of 9 (38.0 mg, 129 μmol, 1.0 equiv) in toluene (2.6 mL) in a Biotage microwave reaction vial (2 5 mL) was added BHT (2.84 mg, 12.9 μmol, 0.1 equiv) and sealed. The reaction mixture was heated under microwave irradiation with an initial 400 W until 140 °C was reached (∼5 min).…”

Section: Experimental Sectionmentioning

confidence: 99%

Synthesis of Highly Functionalized Hydrindanes via Sequential Organocatalytic Michael/Mukaiyama Aldol Addition and Telescoped Hydrozirconation/Cross-Coupling as Key Steps: En Route to the AB System of Clifednamides

et al. 2021

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The AB ring systems of the clifednamide family, polycyclic tetramate macrolactames (PoTeMs), were prepared by a new, convergent approach employing an intramolecular Diels−Alder (IMDA) reaction. Key steps comprise an organocatalytic Michael addition (>90% enantiomeric excess (ee)), a Mukaiyama aldol reaction for the convergent installation of a diene moiety, and a telescoped hydrozirconation/cross-coupling grafting an enone. The following IMDA furnished a highly functionalized hydrindane (diastereomeric ratio (dr) = 91:1) with the same configuration as the clifednamide scaffold. Advantages of this route are only one required protecting group, 13% overall yield over 9 steps (reduced from previously 17 steps/1.3% overall), and the potential access to the key intermediates in the clifednamide biosynthesis.

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“…The final Zn reduction in HOAc gave the naturally occurring (+)-fusarisetin A for the first time. Extra notable synthesis came from Liu et al, highlighting a one-pot-four-step cascade reaction (Scheme 11) [32,62]. The trans-fused decalin aldehyde I, prepared from the triene 74 via an IMDA reaction, underwent an intramolecular Mukaiyama aldol reaction to give the tetracyclic intermediate K, which proceeded through a TMS-deprotection and a PCC oxidation to conveniently provide the tetracyclic compound 75.…”

Section: C3-spiro Ta (Fusarisetin A)mentioning

confidence: 99%

Recent Advances in the Total Synthesis of Tetramic Acid-Containing Natural Products

Bai

Lü

Wang

2016

Journal of Chemistry

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With incredible bioactivities and fascinating structural complexities, tetramic acid- (TA-) containing natural products have attracted favorable attention among the organic chemistry community. Although the construction of the TA core is usually straightforward, the intricate C3-side chain sometimes asks for some deliberative strategy so as to fulfill an elegant total synthesis. This review mainly covers some exceptional synthetic examples for each type of natural product in recent years, showcasing the great achievements as well as unsettled obstacles in this area, in the hope of accelerating the synthetic and biological investigations for this unique type of natural product.

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Total Synthesis of (+)-Fusarisetin A Driven by a One-Pot Four-Reaction Process

Cited by 19 publications

References 55 publications

Synthesis of Allahabadolactone A

Synthesis of Allahabadolactone A

Synthesis of Highly Functionalized Hydrindanes via Sequential Organocatalytic Michael/Mukaiyama Aldol Addition and Telescoped Hydrozirconation/Cross-Coupling as Key Steps: En Route to the AB System of Clifednamides

Recent Advances in the Total Synthesis of Tetramic Acid-Containing Natural Products

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