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Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

ABSTRACT: The synthesis of structurally complex and highly strained natural products provides unique challenges and unexpected opportunities for the development of new reactions and strategies. Herein, the synthesis of (+)-[5]-ladderanoic acid is reported. En route to the target, unusual and unexpected strain release driven transformations were uncovered. This occurrence required a drastic revision of the synthetic design that ultimately led to the development of a novel stepwise cyclobutane assembly by an allylboration/Zweifel olefination sequence.

SUBMITTER: Hancock EN

PROVIDER: S-EPMC6923594 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Hancock Erin N EN Kuker Erin L EL Tantillo Dean J DJ Brown M Kevin MK

Angewandte Chemie (International ed. in English) 20191118 1

The synthesis of structurally complex and highly strained natural products provides unique challenges and unexpected opportunities for the development of new reactions and strategies. Herein, the synthesis of (+)-[5]-ladderanoic acid is reported. En route to the target, unusual and unexpected strain release driven transformations were uncovered. This occurrence required a drastic revision of the synthetic design that ultimately led to the development of a novel stepwise cyclobutane assembly by a ...[more]

PMID: 31650679

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