First total synthesis of the only known 2-isopropyliden-2<em>H</em>-benzofuran-3-one isolated from <em>V. luetzelburgii</em>

Jorgelina L. Pergomet; Enrique L. Larghi; Teodoro S. Kaufman; Andrea B. J. Bracca

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First total synthesis of the only known 2-isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii

机译：从 V分离的唯一已知的2-isopropyliden-2 H -苯并呋喃-3-酮的第一次全合成。 luetzelburgii

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The first total synthesis of 5-(1-hydroxy-1-ethyl)-2-isopropyliden-2H-benzofuran-3-one, is reported in its racemic and in one of its optically active [(S)-(?)] forms. This heterocycle, isolated from Verbesina luetzelburgii, is the only known 2-isopropyliden-2H-benzofuran-3-one produced by species of Verbesina. The sequence took place in eight steps and 19% overall yield (up to 33% for the chiral form), from 4′-hydroxyacetophenone. It entailed carbonyl group protection as the 1,3-dioxolane and a phenol ortho formylation, followed by a Williamson etherification with chloroacetone and an organocatalytic cross-aldolization, to afford a 2-acetyl-2,3-dihydrobenzofuran-3-ol intermediate. The latter underwent a methyl Grignard addition to the carbonyl moiety, followed by selective oxidation of the benzylic alcohol and deprotection, resulting in a β-hydroxy diketone derivative. A MsCl-assisted dehydration of the tertiary alcohol, established the isopropylidene motif, whereas the syntheses culminated by chemical or enzymatic (carrot, celeriac) selective reductions of the exocyclic carbonyl group. 展开▼

机译：据报道，在其外消旋体和其中一种旋光性化合物中，首次合成了5-（1-羟基-1-乙基）-2-异亚丙基-2 H -苯并呋喃-3-酮。（ S ）-（？）]形式。从 Verbesina luetzelburgii 分离的杂环是 Verbesina 物种产生的唯一已知的2-isopropyliden-2 H -苯并呋喃-3-酮。该序列分八步进行，得自4'-羟基苯乙酮，总产率为19％（手性形式最高为33％）。它需要1,3-二氧戊环和苯酚的邻甲酰基甲酰基化，然后用氯丙酮进行威廉姆森醚化和有机催化的交叉醛基化，以得到2-乙酰基-2,3-羰基化，从而保护羰基。二氢苯并呋喃-3-醇中间体。后者在羰基部分上进行了甲基格利雅（Grignard）加成反应，随后对苄醇进行选择性氧化并脱保护，得到β-羟基二酮衍生物。 MsCl辅助的叔醇脱水建立了异亚丙基基序，而合成过程则是通过化学或酶促（胡萝卜，芹菜素）选择性还原外环羰基而达到的。 展开▼

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《RSC Advances》 |2017年第9期|共9页

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Jorgelina L. Pergomet; Enrique L. Larghi; Teodoro S. Kaufman; Andrea B. J. Bracca;
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First total synthesis of the only known 2-isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii

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