Stereodivergent Synthesis of (+)- and (−)-Isolineatin

Abstract

A stereodivergent approach to (+)- and (-)-isolineatin using (S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone as the single source of asymmetry by exploiting the inherent chirality at the C-5 stereocenter is described.

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

“… 531 In the last two decades, Alibés, Figueredo, Font, and co-workers widely employed free and oxygen-protected 5-hydroxymethyl-2(5 H )-furanones. 532 − 539 Significant diastereoselectivities were recorded in several intermolecular [2 + 2] photocycloaddition reactions, and numerous applications were disclosed for the enantioselective synthesis of terpenoid natural products 540 − 545 and new nucleoside analogues ( Scheme 96 ). 546 − 549 …”

“…The facial diastereoselectivity in intermolecular [2 + 2] photocycloaddition reactions of 2­(5 H )-furanones is variable and depends on the nature of the substituent in the 5-position and on the olefinic component . In the last two decades, Alibés, Figueredo, Font, and co-workers widely employed free and oxygen-protected 5-hydroxymethyl-2­(5 H )-furanones. − Significant diastereoselectivities were recorded in several intermolecular [2 + 2] photocycloaddition reactions, and numerous applications were disclosed for the enantioselective synthesis of terpenoid natural products − and new nucleoside analogues (Scheme ). − …”

Lewis base‐catalyzed electrophilic lactonization of selenyl bromide resin and facile solid‐phase synthesis of furan‐2(5H)‐one derivatives

“…). Furthermore, relatively simple furan‐2(5 H )‐one derivatives are also useful as synthetic intermediates in the preparation of bioactive compounds …”

Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure

“…2(5 H )‐Furanone moiety is frequently found in many natural products with biological activities, and some simple 2(5 H )‐furanone molecules are important intermediates in asymmetric organic synthesis . These make increasing great amounts of importance attached to the 2(5 H )‐furanone chemistry recently .…”

“…[ 15,[17][18][19] 2(5 H )-Furanone moiety is frequently found in many natural products with biological activities, [20][21][22] and some simple 2(5 H )-furanone molecules are important intermediates in asymmetric organic synthesis. [23][24][25] These make increasing great amounts of importance attached to the 2(5 H )-furanone chemistry recently. [26][27][28] However, there is no report on the synthesis of chiral PDAs with 2(5 H )furanone moiety before.…”