Total Synthesis of (-)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol

Ian Paterson; Michael V. Perkins

doi:10.1016/0040-4020(95)01015-7

Total Synthesis of (-)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol

Ian Paterson
, Michael V. Perkins

Research output: Contribution to journal › Article › peer-review

78 Citations (Scopus)

Abstract

The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C₁₀ in 35 led to (-)-denticulatin A (1).

Original language	English
Pages (from-to)	1811-1834
Number of pages	24
Journal	Tetrahedron
Volume	52
Issue number	5
DOIs	https://doi.org/10.1016/0040-4020(95)01015-7
Publication status	Published - 29 Jan 1996
Externally published	Yes

Access to Document

10.1016/0040-4020(95)01015-7Licence: In Copyright

Cite this

@article{ace7e7fcc63b428e828fff629a9b02fb,

title = "Total Synthesis of (-)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol",

abstract = "The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20\% yield), with 70\% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).",

author = "Ian Paterson and Perkins, \{Michael V.\}",

year = "1996",

month = jan,

day = "29",

doi = "10.1016/0040-4020(95)01015-7",

language = "English",

volume = "52",

pages = "1811--1834",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "5",

}

TY - JOUR

T1 - Total Synthesis of (-)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol

AU - Paterson, Ian

AU - Perkins, Michael V.

PY - 1996/1/29

Y1 - 1996/1/29

N2 - The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).

AB - The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).

UR - https://www.scopus.com/pages/publications/0030041247

U2 - 10.1016/0040-4020(95)01015-7

DO - 10.1016/0040-4020(95)01015-7

M3 - Article

AN - SCOPUS:0030041247

SN - 0040-4020

VL - 52

SP - 1811

EP - 1834

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

Total Synthesis of (-)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol

Abstract

Access to Document

Other files and links

Fingerprint

Cite this