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Stereoselective Construction of C 2-Symmetric Adjacent Bis-α,α′-cis-Disubstituted THF Skeleton via Double Intramolecular Amide Enolate Alkylation: Total Syntheses of (+)-Membranacin and (+)-Squamocin-N
- Batthula, Srinivas;
- Sanapalli, Sudharshan Reddy;
- Samala, Mallesham;
- Rapelli, Chandrashekhar;
- Kwak, Minjung;
- ... Kim, Seok Ho;
- ... Lee, Jongkook;
- 외 2명
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Described herein is the highly stereoselective and concise first asymmetric total synthesis of (+)-squamocin-N (1b) bearing a C15-C24 adjacent bis-tetrahydrofuran (THF) backbone with threo/cis/threo/cis/threo stereochemistry. This approach features construction of C 2-symmetric adjacent cis/threo/cis bis-THF core 5 via a novel double intramolecular amide enolate alkylation (IAEA) protocol, reductive desymmetrization of C 2-symmetric bis-THF 5, and chelation-controlled nucleophilic addition (CCNA) as the key steps. In addition, (+)-membranacin (1a), the C24 epimer of 1b, was synthesized via Mitsunobu inversion.
키워드
ANNONACEOUS ACETOGENINS; SEEDS; ROLLINIASTATIN-1; STEREOCHEMISTRY; CYCLIZATION; UVARICIN; H-1-NMR; COMPLEX; MOIETY; THREO
- 제목
- Stereoselective Construction of C 2-Symmetric Adjacent Bis-α,α′-cis-Disubstituted THF Skeleton via Double Intramolecular Amide Enolate Alkylation: Total Syntheses of (+)-Membranacin and (+)-Squamocin-N
- 저자
- Batthula, Srinivas; Sanapalli, Sudharshan Reddy; Samala, Mallesham; Rapelli, Chandrashekhar; Kwak, Minjung; Yalavarthi, Nageswarao; Kim, Seok Ho; Kim, Deukjoon; Lee, Jongkook
- 발행일
- 2026-01-16
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 28
- 호
- 2
- 페이지
- 860 ~ 865