Synthesis of benzoquinones and annulated derivatives from conjugated ketenes
TL;DR: Synthese de benzoquinones-1,4, naphtoquinones -1, 4, benzofurannediones-4, 7 et benzo [b] thiophenediones -4,7 a partir de cyclobutene-2ones
Abstract: Synthese de benzoquinones-1,4, naphtoquinones-1,4, benzofurannediones-4,7 et benzo [b] thiophenediones-4,7 a partir de cyclobutene-2ones
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TL;DR: Transformation of Cyclobutane Derivatives inNatural Product Syntheses: A Review of the Transformations in Organic Syntheses.
Abstract: I. Introduction 1485II. Scope of This Review 1485III. Transformations of Cyclobutane Derivatives inOrganic Syntheses1486A. Ring-Opening Reactions 1486B. Ring-Contraction Reactions 1493C. Ring-Expansion Reactions 14951. Five-Membered Rings 14952. Six-Membered Rings 15093. Seven-Membered Rings 15174. Eight-Membered Rings 15215. Nine-Membered Rings 1523IV. Transformations of Cyclobutane Derivatives inNatural Product Syntheses1524A. Ring-Opening Reactions 1524B. Ring-Expansion Reactions 15261. Five-Membered Rings 15262. Six-Membered Rings 15293. Seven-Membered Rings 15324. Eight-Membered Rings 1533V. Conclusion 1534VI. Acknowledgments 1534VII. References 1534
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TL;DR: A modular approach to the total synthesis of fURAquinocins culminated in the total syntheses of furaquinocin A, B, and E.
Abstract: A modular approach to the total synthesis of furaquinocins culminated in the total syntheses of furaquinocin A, B, and E. A Pd-catalyzed dynamic kinetic asymmetric transformation (DYKAT) on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck cyclization allows the enantio- and diastereoselective construction of dihydrobenzofuran 32. Introduction of a double unsatured side chain via Horner-Wadsworth-Emmons reaction and assembly of the naphthoquinone with squaric acid based methodology leads to furaquinocin E. The use of differentially substituted squaric acid derivatives allows the synthesis of three analogues of furaquinocin E. The additional stereocenters in furaquinocin A and B can be introduced with a diastereoselective Sakurai allylation. The stereoselective elongation of the side chain is possible using cross metathesis or ring closing metathesis. The obtained late-stage intermediates were successfully transformed to furaquinocin A and B.
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